Cas no 83945-57-7 (1-Naphthalenecarboxylic acid,decahydro-1,4a-dimethyl-6-methylene-5-[(2E)-3-methyl-2,4-pentadienyl]-, (1R,4aR,5S,8aR)-)

1-Naphthalenecarboxylic acid,decahydro-1,4a-dimethyl-6-methylene-5-[(2E)-3-methyl-2,4-pentadienyl]-, (1R,4aR,5S,8aR)- structure
83945-57-7 structure
Product Name:1-Naphthalenecarboxylic acid,decahydro-1,4a-dimethyl-6-methylene-5-[(2E)-3-methyl-2,4-pentadienyl]-, (1R,4aR,5S,8aR)-
CAS No:83945-57-7
MF:C20H30O2
MW:302.451006412506
CID:836833
PubChem ID:12303813
Update Time:2024-10-26

1-Naphthalenecarboxylic acid,decahydro-1,4a-dimethyl-6-methylene-5-[(2E)-3-methyl-2,4-pentadienyl]-, (1R,4aR,5S,8aR)- Chemical and Physical Properties

Names and Identifiers

    • 1-Naphthalenecarboxylic acid, decahydro-1,4a-dimethyl-6-methylene-5-[(2E)-3-methyl-2,4-pentadienyl ]-, (1R,4aR,5S,8aR)-
    • 4-Epicommunic acid
    • (1R,4aR,5S,8aR)-1,4a-Dimethyl-6-methylene-5-[(2E)-3-methyl-2,4-pe ntadien-1-yl]decahydro-1-naphthalenecarboxylic acid
    • Labda-8(17)
    • [ "Labda-8(17)", "12E", "14-trien-18-oic acid" ]
    • (1R,4aR,5S,8aR)-Decahydro-1,4a-dimethyl-6-methylene-5-[(2E)-3-methyl-2,4-pentadien-1-yl]-1-naphthalenecarboxylic acid (ACI)
    • 1-Naphthalenecarboxylic acid, decahydro-1,4a-dimethyl-6-methylene-5-(3-methyl-2,4-pentadienyl)-, [1R-[1α,4aβ,5β(E),8aα]]- (ZCI)
    • 1-Naphthalenecarboxylic acid, decahydro-1,4a-dimethyl-6-methylene-5-[(2E)-3-methyl-2,4-pentadienyl]-, (1R,4aR,5S,8aR)- (9CI)
    • (+)-trans-Ozic acid
    • 4-epi-trans-Communic acid
    • trans-Ozic acid
    • (1R,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[(2E)-3-methylpenta-2,4-dienyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
    • CHEMBL3402737
    • FS-9087
    • (+)-trans-Ozic acid; 4-epi-trans-Communic acid
    • (1R,4AR,5S,8aR)-1,4a-dimethyl-6-methylene-5-((E)-3-methylpenta-2,4-dien-1-yl)decahydronaphthalene-1-carboxylic acid
    • AKOS040761135
    • 83945-57-7
    • 1-Naphthalenecarboxylic acid,decahydro-1,4a-dimethyl-6-methylene-5-[(2E)-3-methyl-2,4-pentadienyl]-, (1R,4aR,5S,8aR)-
    • Inchi： 1S/C20H30O2/c1-6-14(2)8-10-16-15(3)9-11-17-19(16,4)12-7-13-20(17,5)18(21)22/h6,8,16-17H,1,3,7,9-13H2,2,4-5H3,(H,21,22)/b14-8+/t16-,17+,19+,20+/m0/s1
    • InChI Key： YGBZFOQXPOGACY-ONIUZDBUSA-N
    • SMILES： C[C@@]12[C@@H](C/C=C(\C)/C=C)C(=C)CC[C@H]1[C@](CCC2)(C)C(=O)O

Computed Properties

  • Exact Mass: 302.22500
  • Monoisotopic Mass: 302.224580195g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 22
  • Rotatable Bond Count: 4
  • Complexity: 516
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 4
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 5.7
  • Topological Polar Surface Area: 37.3?2

Experimental Properties

  • Color/Form: Powder
  • Density: 1.3±0.1 g/cm3
  • Boiling Point: 271.7±40.0 °C at 760 mmHg
  • Flash Point: 144.3±12.9 °C
  • PSA: 37.30000
  • LogP: 5.37230
  • Vapor Pressure: 0.0±0.5 mmHg at 25°C

1-Naphthalenecarboxylic acid,decahydro-1,4a-dimethyl-6-methylene-5-[(2E)-3-methyl-2,4-pentadienyl]-, (1R,4aR,5S,8aR)- Security Information

1-Naphthalenecarboxylic acid,decahydro-1,4a-dimethyl-6-methylene-5-[(2E)-3-methyl-2,4-pentadienyl]-, (1R,4aR,5S,8aR)- Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
SHANG HAI JI ZHI SHENG HUA Technology Co., Ltd.
E12800-5mg
(1R,4aR,5S,8aR)-1,4a-Dimethyl-6-methylene-5-[(2E)-3-methyl-2,4-pe ntadien-1-yl]decahydro-1-naphthalenecarboxylic acid
 83945-57-7 ,HPLC≥98%
5mg
 ￥3438.0 2023-09-08
TargetMol Chemicals
TN3028-1 ml * 10 mm
4-Epicommunic acid
 83945-57-7
1 ml * 10 mm
 ￥ 3430 2024-07-20
TargetMol Chemicals
TN3028-5 mg
4-Epicommunic acid
 83945-57-7 98%
5mg
 ￥ 3,330 2023-07-11
TargetMol Chemicals
TN3028-1 mL * 10 mM (in DMSO)
4-Epicommunic acid
 83945-57-7 98%
1 mL * 10 mM (in DMSO)
 ￥ 3430 2023-09-15
TargetMol Chemicals
TN3028-5mg
4-Epicommunic acid
 83945-57-7
5mg
 ￥ 3330 2024-07-20

1-Naphthalenecarboxylic acid,decahydro-1,4a-dimethyl-6-methylene-5-[(2E)-3-methyl-2,4-pentadienyl]-, (1R,4aR,5S,8aR)- Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Potassium hydroxide ,  Lithium hydroxide Solvents: Methanol ,  Water ;  24 h, reflux; reflux → rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, rt
Reference
A chiral pool approach for asymmetric syntheses of (-)-antrocin, (+)-asperolide C, and (-)-trans-ozic acid
Li, Fu-Zhuo; et al, Chemical Communications (Cambridge, 2016, 52(84), 12426-12429

Production Method 2

Reaction Conditions
1.1 Reagents: 2-Methyl-2-butene ,  Sodium chlorite Catalysts: 2-Azatricyclo[3.3.1.13,7]dec-2-yloxy Solvents: Acetic acid ,  Dichloromethane ,  Water ;  24 h, pH 4.6, rt
1.2 Reagents: Sodium bisulfite Solvents: Water
Reference
Total Synthesis of Taiwaniadducts B, C, and D
Deng, Jun; et al, Journal of the American Chemical Society, 2014, 136(23), 8185-8188

Production Method 3

Reaction Conditions
1.1 Solvents: Toluene ;  22 °C → 110 °C; 22 h, 110 °C
2.1 Reagents: Butyllithium Solvents: Hexane ;  30 min, 0 °C; 0 °C → -78 °C
2.2 Solvents: Tetrahydrofuran ;  1 h, -78 °C
2.3 Reagents: Sodium bicarbonate Solvents: Water
3.1 Reagents: 2-Methyl-2-butene ,  Sodium chlorite Catalysts: 2-Azatricyclo[3.3.1.13,7]dec-2-yloxy Solvents: Acetic acid ,  Dichloromethane ,  Water ;  24 h, pH 4.6, rt
3.2 Reagents: Sodium bisulfite Solvents: Water
Reference
Total Synthesis of Taiwaniadducts B, C, and D
Deng, Jun; et al, Journal of the American Chemical Society, 2014, 136(23), 8185-8188

Production Method 4

Reaction Conditions
1.1 Solvents: Toluene ;  rt; 24 h, 110 °C
2.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ;  1 h, 0 °C
2.2 Solvents: Tetrahydrofuran ;  0 °C → rt; 2 h, rt
2.3 Reagents: Ammonium chloride Solvents: Water ;  rt
3.1 Reagents: Potassium hydroxide ,  Lithium hydroxide Solvents: Methanol ,  Water ;  24 h, reflux; reflux → rt
3.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, rt
Reference
A chiral pool approach for asymmetric syntheses of (-)-antrocin, (+)-asperolide C, and (-)-trans-ozic acid
Li, Fu-Zhuo; et al, Chemical Communications (Cambridge, 2016, 52(84), 12426-12429

Production Method 5

Reaction Conditions
1.1 Reagents: Triethylsilane Catalysts: Palladium ,  Water Solvents: Tetrahydrofuran ;  overnight, rt
2.1 Solvents: Toluene ;  rt; 24 h, 110 °C
3.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ;  1 h, 0 °C
3.2 Solvents: Tetrahydrofuran ;  0 °C → rt; 2 h, rt
3.3 Reagents: Ammonium chloride Solvents: Water ;  rt
4.1 Reagents: Potassium hydroxide ,  Lithium hydroxide Solvents: Methanol ,  Water ;  24 h, reflux; reflux → rt
4.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, rt
Reference
A chiral pool approach for asymmetric syntheses of (-)-antrocin, (+)-asperolide C, and (-)-trans-ozic acid
Li, Fu-Zhuo; et al, Chemical Communications (Cambridge, 2016, 52(84), 12426-12429

Production Method 6

Reaction Conditions
1.1 Reagents: Pyridine ,  Thionyl chloride Solvents: Dichloromethane ;  1 h, -78 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water
2.1 Reagents: Diisobutylaluminum hydride Solvents: Tetrahydrofuran ;  1 h, -78 °C
2.2 Reagents: Hydrochloric acid Solvents: Water
3.1 Solvents: Toluene ;  22 °C → 110 °C; 22 h, 110 °C
4.1 Reagents: Butyllithium Solvents: Hexane ;  30 min, 0 °C; 0 °C → -78 °C
4.2 Solvents: Tetrahydrofuran ;  1 h, -78 °C
4.3 Reagents: Sodium bicarbonate Solvents: Water
5.1 Reagents: 2-Methyl-2-butene ,  Sodium chlorite Catalysts: 2-Azatricyclo[3.3.1.13,7]dec-2-yloxy Solvents: Acetic acid ,  Dichloromethane ,  Water ;  24 h, pH 4.6, rt
5.2 Reagents: Sodium bisulfite Solvents: Water
Reference
Total Synthesis of Taiwaniadducts B, C, and D
Deng, Jun; et al, Journal of the American Chemical Society, 2014, 136(23), 8185-8188

Production Method 7

Reaction Conditions
1.1 Reagents: 1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  0 °C → rt; overnight, rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  rt
2.1 Reagents: Triethylsilane Catalysts: Palladium ,  Water Solvents: Tetrahydrofuran ;  overnight, rt
3.1 Solvents: Toluene ;  rt; 24 h, 110 °C
4.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ;  1 h, 0 °C
4.2 Solvents: Tetrahydrofuran ;  0 °C → rt; 2 h, rt
4.3 Reagents: Ammonium chloride Solvents: Water ;  rt
5.1 Reagents: Potassium hydroxide ,  Lithium hydroxide Solvents: Methanol ,  Water ;  24 h, reflux; reflux → rt
5.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, rt
Reference
A chiral pool approach for asymmetric syntheses of (-)-antrocin, (+)-asperolide C, and (-)-trans-ozic acid
Li, Fu-Zhuo; et al, Chemical Communications (Cambridge, 2016, 52(84), 12426-12429

Production Method 8

Reaction Conditions
1.1 Reagents: 1,1,1,3,3,3-Hexafluoro-2-propanol ,  2,3-Benzodioxin-1,4-dione ;  rt; 12 h, 40 °C; 40 °C → rt
1.2 Reagents: Sodium bicarbonate Solvents: Methanol ,  Water ;  6 h, 40 °C
1.3 Solvents: Water ;  pH 7
2.1 Reagents: Ozone Solvents: Methanol ,  Dichloromethane ;  1.5 h, -78 °C
2.2 Reagents: Zinc Solvents: Acetic acid ;  2.5 h, rt
2.3 Reagents: 1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  0 °C → rt; overnight, rt
2.4 Reagents: Ammonium chloride Solvents: Water ;  rt
3.1 Reagents: Triethylsilane Catalysts: Palladium ,  Water Solvents: Tetrahydrofuran ;  overnight, rt
4.1 Solvents: Toluene ;  rt; 24 h, 110 °C
5.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ;  1 h, 0 °C
5.2 Solvents: Tetrahydrofuran ;  0 °C → rt; 2 h, rt
5.3 Reagents: Ammonium chloride Solvents: Water ;  rt
6.1 Reagents: Potassium hydroxide ,  Lithium hydroxide Solvents: Methanol ,  Water ;  24 h, reflux; reflux → rt
6.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, rt
Reference
A chiral pool approach for asymmetric syntheses of (-)-antrocin, (+)-asperolide C, and (-)-trans-ozic acid
Li, Fu-Zhuo; et al, Chemical Communications (Cambridge, 2016, 52(84), 12426-12429

Production Method 9

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Acetone ;  overnight, rt
2.1 Reagents: 1,1,1,3,3,3-Hexafluoro-2-propanol ,  2,3-Benzodioxin-1,4-dione ;  rt; 12 h, 40 °C; 40 °C → rt
2.2 Reagents: Sodium bicarbonate Solvents: Methanol ,  Water ;  6 h, 40 °C
2.3 Solvents: Water ;  pH 7
3.1 Reagents: Ozone Solvents: Methanol ,  Dichloromethane ;  1.5 h, -78 °C
3.2 Reagents: Zinc Solvents: Acetic acid ;  2.5 h, rt
3.3 Reagents: 1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  0 °C → rt; overnight, rt
3.4 Reagents: Ammonium chloride Solvents: Water ;  rt
4.1 Reagents: Triethylsilane Catalysts: Palladium ,  Water Solvents: Tetrahydrofuran ;  overnight, rt
5.1 Solvents: Toluene ;  rt; 24 h, 110 °C
6.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ;  1 h, 0 °C
6.2 Solvents: Tetrahydrofuran ;  0 °C → rt; 2 h, rt
6.3 Reagents: Ammonium chloride Solvents: Water ;  rt
7.1 Reagents: Potassium hydroxide ,  Lithium hydroxide Solvents: Methanol ,  Water ;  24 h, reflux; reflux → rt
7.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, rt
Reference
A chiral pool approach for asymmetric syntheses of (-)-antrocin, (+)-asperolide C, and (-)-trans-ozic acid
Li, Fu-Zhuo; et al, Chemical Communications (Cambridge, 2016, 52(84), 12426-12429

Production Method 10

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ;  1 h, 0 °C
1.2 Solvents: Tetrahydrofuran ;  0 °C → rt; 2 h, rt
1.3 Reagents: Ammonium chloride Solvents: Water ;  rt
2.1 Reagents: Potassium hydroxide ,  Lithium hydroxide Solvents: Methanol ,  Water ;  24 h, reflux; reflux → rt
2.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, rt
Reference
A chiral pool approach for asymmetric syntheses of (-)-antrocin, (+)-asperolide C, and (-)-trans-ozic acid
Li, Fu-Zhuo; et al, Chemical Communications (Cambridge, 2016, 52(84), 12426-12429

Production Method 11

Reaction Conditions
1.1 Reagents: Butyllithium Solvents: Hexane ;  30 min, 0 °C; 0 °C → -78 °C
1.2 Solvents: Tetrahydrofuran ;  1 h, -78 °C
1.3 Reagents: Sodium bicarbonate Solvents: Water
2.1 Reagents: 2-Methyl-2-butene ,  Sodium chlorite Catalysts: 2-Azatricyclo[3.3.1.13,7]dec-2-yloxy Solvents: Acetic acid ,  Dichloromethane ,  Water ;  24 h, pH 4.6, rt
2.2 Reagents: Sodium bisulfite Solvents: Water
Reference
Total Synthesis of Taiwaniadducts B, C, and D
Deng, Jun; et al, Journal of the American Chemical Society, 2014, 136(23), 8185-8188

Production Method 12

Reaction Conditions
1.1 Reagents: Diisobutylaluminum hydride Solvents: Tetrahydrofuran ;  1 h, -78 °C
1.2 Reagents: Hydrochloric acid Solvents: Water
2.1 Solvents: Toluene ;  22 °C → 110 °C; 22 h, 110 °C
3.1 Reagents: Butyllithium Solvents: Hexane ;  30 min, 0 °C; 0 °C → -78 °C
3.2 Solvents: Tetrahydrofuran ;  1 h, -78 °C
3.3 Reagents: Sodium bicarbonate Solvents: Water
4.1 Reagents: 2-Methyl-2-butene ,  Sodium chlorite Catalysts: 2-Azatricyclo[3.3.1.13,7]dec-2-yloxy Solvents: Acetic acid ,  Dichloromethane ,  Water ;  24 h, pH 4.6, rt
4.2 Reagents: Sodium bisulfite Solvents: Water
Reference
Total Synthesis of Taiwaniadducts B, C, and D
Deng, Jun; et al, Journal of the American Chemical Society, 2014, 136(23), 8185-8188

Production Method 13

Reaction Conditions
1.1 Reagents: Ozone Solvents: Methanol ,  Dichloromethane ;  1.5 h, -78 °C
1.2 Reagents: Zinc Solvents: Acetic acid ;  2.5 h, rt
1.3 Reagents: 1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  0 °C → rt; overnight, rt
1.4 Reagents: Ammonium chloride Solvents: Water ;  rt
2.1 Reagents: Triethylsilane Catalysts: Palladium ,  Water Solvents: Tetrahydrofuran ;  overnight, rt
3.1 Solvents: Toluene ;  rt; 24 h, 110 °C
4.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ;  1 h, 0 °C
4.2 Solvents: Tetrahydrofuran ;  0 °C → rt; 2 h, rt
4.3 Reagents: Ammonium chloride Solvents: Water ;  rt
5.1 Reagents: Potassium hydroxide ,  Lithium hydroxide Solvents: Methanol ,  Water ;  24 h, reflux; reflux → rt
5.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, rt
Reference
A chiral pool approach for asymmetric syntheses of (-)-antrocin, (+)-asperolide C, and (-)-trans-ozic acid
Li, Fu-Zhuo; et al, Chemical Communications (Cambridge, 2016, 52(84), 12426-12429

Production Method 14

Reaction Conditions
1.1 Reagents: Ozone Solvents: Methanol ,  Dichloromethane ;  1.5 h, -78 °C
1.2 Reagents: Zinc Solvents: Acetic acid ;  2.5 h, rt
2.1 Reagents: 1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  0 °C → rt; overnight, rt
2.2 Reagents: Ammonium chloride Solvents: Water ;  rt
3.1 Reagents: Triethylsilane Catalysts: Palladium ,  Water Solvents: Tetrahydrofuran ;  overnight, rt
4.1 Solvents: Toluene ;  rt; 24 h, 110 °C
5.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ;  1 h, 0 °C
5.2 Solvents: Tetrahydrofuran ;  0 °C → rt; 2 h, rt
5.3 Reagents: Ammonium chloride Solvents: Water ;  rt
6.1 Reagents: Potassium hydroxide ,  Lithium hydroxide Solvents: Methanol ,  Water ;  24 h, reflux; reflux → rt
6.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, rt
Reference
A chiral pool approach for asymmetric syntheses of (-)-antrocin, (+)-asperolide C, and (-)-trans-ozic acid
Li, Fu-Zhuo; et al, Chemical Communications (Cambridge, 2016, 52(84), 12426-12429

Production Method 15

Reaction Conditions
1.1 Reagents: Chloro(1-methylethyl)magnesium Solvents: Tetrahydrofuran ;  -78 °C → 0 °C; 30 min, 0 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water
2.1 Reagents: Pyridine ,  Thionyl chloride Solvents: Dichloromethane ;  1 h, -78 °C
2.2 Reagents: Sodium bicarbonate Solvents: Water
3.1 Reagents: Diisobutylaluminum hydride Solvents: Tetrahydrofuran ;  1 h, -78 °C
3.2 Reagents: Hydrochloric acid Solvents: Water
4.1 Solvents: Toluene ;  22 °C → 110 °C; 22 h, 110 °C
5.1 Reagents: Butyllithium Solvents: Hexane ;  30 min, 0 °C; 0 °C → -78 °C
5.2 Solvents: Tetrahydrofuran ;  1 h, -78 °C
5.3 Reagents: Sodium bicarbonate Solvents: Water
6.1 Reagents: 2-Methyl-2-butene ,  Sodium chlorite Catalysts: 2-Azatricyclo[3.3.1.13,7]dec-2-yloxy Solvents: Acetic acid ,  Dichloromethane ,  Water ;  24 h, pH 4.6, rt
6.2 Reagents: Sodium bisulfite Solvents: Water
Reference
Total Synthesis of Taiwaniadducts B, C, and D
Deng, Jun; et al, Journal of the American Chemical Society, 2014, 136(23), 8185-8188

Production Method 16

Reaction Conditions
1.1 Reagents: Sodium periodate ,  Ruthenium trichloride Solvents: Carbon tetrachloride ,  Acetonitrile ,  Water ;  2 h, pH 7, 22 °C
2.1 Reagents: Chloro(1-methylethyl)magnesium Solvents: Tetrahydrofuran ;  -78 °C → 0 °C; 30 min, 0 °C
2.2 Reagents: Sodium bicarbonate Solvents: Water
3.1 Reagents: Pyridine ,  Thionyl chloride Solvents: Dichloromethane ;  1 h, -78 °C
3.2 Reagents: Sodium bicarbonate Solvents: Water
4.1 Reagents: Diisobutylaluminum hydride Solvents: Tetrahydrofuran ;  1 h, -78 °C
4.2 Reagents: Hydrochloric acid Solvents: Water
5.1 Solvents: Toluene ;  22 °C → 110 °C; 22 h, 110 °C
6.1 Reagents: Butyllithium Solvents: Hexane ;  30 min, 0 °C; 0 °C → -78 °C
6.2 Solvents: Tetrahydrofuran ;  1 h, -78 °C
6.3 Reagents: Sodium bicarbonate Solvents: Water
7.1 Reagents: 2-Methyl-2-butene ,  Sodium chlorite Catalysts: 2-Azatricyclo[3.3.1.13,7]dec-2-yloxy Solvents: Acetic acid ,  Dichloromethane ,  Water ;  24 h, pH 4.6, rt
7.2 Reagents: Sodium bisulfite Solvents: Water
Reference
Total Synthesis of Taiwaniadducts B, C, and D
Deng, Jun; et al, Journal of the American Chemical Society, 2014, 136(23), 8185-8188

Production Method 17

Reaction Conditions
1.1 Reagents: Hydrazine Solvents: Diethylene glycol ;  22 °C → 160 °C; 2 h, 160 °C; 160 °C → 22 °C
1.2 Reagents: Potassium hydroxide ;  22 °C → 180 °C; 4 h, 180 °C; 180 °C → 22 °C
1.3 Reagents: Hydrochloric acid Solvents: Water
2.1 Reagents: Sodium periodate ,  Ruthenium trichloride Solvents: Carbon tetrachloride ,  Acetonitrile ,  Water ;  2 h, pH 7, 22 °C
3.1 Reagents: Chloro(1-methylethyl)magnesium Solvents: Tetrahydrofuran ;  -78 °C → 0 °C; 30 min, 0 °C
3.2 Reagents: Sodium bicarbonate Solvents: Water
4.1 Reagents: Pyridine ,  Thionyl chloride Solvents: Dichloromethane ;  1 h, -78 °C
4.2 Reagents: Sodium bicarbonate Solvents: Water
5.1 Reagents: Diisobutylaluminum hydride Solvents: Tetrahydrofuran ;  1 h, -78 °C
5.2 Reagents: Hydrochloric acid Solvents: Water
6.1 Solvents: Toluene ;  22 °C → 110 °C; 22 h, 110 °C
7.1 Reagents: Butyllithium Solvents: Hexane ;  30 min, 0 °C; 0 °C → -78 °C
7.2 Solvents: Tetrahydrofuran ;  1 h, -78 °C
7.3 Reagents: Sodium bicarbonate Solvents: Water
8.1 Reagents: 2-Methyl-2-butene ,  Sodium chlorite Catalysts: 2-Azatricyclo[3.3.1.13,7]dec-2-yloxy Solvents: Acetic acid ,  Dichloromethane ,  Water ;  24 h, pH 4.6, rt
8.2 Reagents: Sodium bisulfite Solvents: Water
Reference
Total Synthesis of Taiwaniadducts B, C, and D
Deng, Jun; et al, Journal of the American Chemical Society, 2014, 136(23), 8185-8188

Production Method 18

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide Solvents: tert-Butanol ;  15 min, 22 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water
1.3 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  1 h, 22 °C
2.1 Reagents: Hydrazine Solvents: Diethylene glycol ;  22 °C → 160 °C; 2 h, 160 °C; 160 °C → 22 °C
2.2 Reagents: Potassium hydroxide ;  22 °C → 180 °C; 4 h, 180 °C; 180 °C → 22 °C
2.3 Reagents: Hydrochloric acid Solvents: Water
3.1 Reagents: Sodium periodate ,  Ruthenium trichloride Solvents: Carbon tetrachloride ,  Acetonitrile ,  Water ;  2 h, pH 7, 22 °C
4.1 Reagents: Chloro(1-methylethyl)magnesium Solvents: Tetrahydrofuran ;  -78 °C → 0 °C; 30 min, 0 °C
4.2 Reagents: Sodium bicarbonate Solvents: Water
5.1 Reagents: Pyridine ,  Thionyl chloride Solvents: Dichloromethane ;  1 h, -78 °C
5.2 Reagents: Sodium bicarbonate Solvents: Water
6.1 Reagents: Diisobutylaluminum hydride Solvents: Tetrahydrofuran ;  1 h, -78 °C
6.2 Reagents: Hydrochloric acid Solvents: Water
7.1 Solvents: Toluene ;  22 °C → 110 °C; 22 h, 110 °C
8.1 Reagents: Butyllithium Solvents: Hexane ;  30 min, 0 °C; 0 °C → -78 °C
8.2 Solvents: Tetrahydrofuran ;  1 h, -78 °C
8.3 Reagents: Sodium bicarbonate Solvents: Water
9.1 Reagents: 2-Methyl-2-butene ,  Sodium chlorite Catalysts: 2-Azatricyclo[3.3.1.13,7]dec-2-yloxy Solvents: Acetic acid ,  Dichloromethane ,  Water ;  24 h, pH 4.6, rt
9.2 Reagents: Sodium bisulfite Solvents: Water
Reference
Total Synthesis of Taiwaniadducts B, C, and D
Deng, Jun; et al, Journal of the American Chemical Society, 2014, 136(23), 8185-8188

Production Method 19

Reaction Conditions
1.1 Reagents: Ozone Solvents: Dichloromethane ;  -78 °C
1.2 Reagents: Triphenylphosphine ;  -78 °C → 22 °C; 4 h, 22 °C
2.1 Reagents: Potassium tert-butoxide Solvents: tert-Butanol ;  15 min, 22 °C
2.2 Reagents: Sodium bicarbonate Solvents: Water
2.3 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  1 h, 22 °C
3.1 Reagents: Hydrazine Solvents: Diethylene glycol ;  22 °C → 160 °C; 2 h, 160 °C; 160 °C → 22 °C
3.2 Reagents: Potassium hydroxide ;  22 °C → 180 °C; 4 h, 180 °C; 180 °C → 22 °C
3.3 Reagents: Hydrochloric acid Solvents: Water
4.1 Reagents: Sodium periodate ,  Ruthenium trichloride Solvents: Carbon tetrachloride ,  Acetonitrile ,  Water ;  2 h, pH 7, 22 °C
5.1 Reagents: Chloro(1-methylethyl)magnesium Solvents: Tetrahydrofuran ;  -78 °C → 0 °C; 30 min, 0 °C
5.2 Reagents: Sodium bicarbonate Solvents: Water
6.1 Reagents: Pyridine ,  Thionyl chloride Solvents: Dichloromethane ;  1 h, -78 °C
6.2 Reagents: Sodium bicarbonate Solvents: Water
7.1 Reagents: Diisobutylaluminum hydride Solvents: Tetrahydrofuran ;  1 h, -78 °C
7.2 Reagents: Hydrochloric acid Solvents: Water
8.1 Solvents: Toluene ;  22 °C → 110 °C; 22 h, 110 °C
9.1 Reagents: Butyllithium Solvents: Hexane ;  30 min, 0 °C; 0 °C → -78 °C
9.2 Solvents: Tetrahydrofuran ;  1 h, -78 °C
9.3 Reagents: Sodium bicarbonate Solvents: Water
10.1 Reagents: 2-Methyl-2-butene ,  Sodium chlorite Catalysts: 2-Azatricyclo[3.3.1.13,7]dec-2-yloxy Solvents: Acetic acid ,  Dichloromethane ,  Water ;  24 h, pH 4.6, rt
10.2 Reagents: Sodium bisulfite Solvents: Water
Reference
Total Synthesis of Taiwaniadducts B, C, and D
Deng, Jun; et al, Journal of the American Chemical Society, 2014, 136(23), 8185-8188

Production Method 20

Reaction Conditions
1.1 Reagents: Boron trifluoride etherate Solvents: Dichloromethane ;  0 °C → 22 °C; 2.5 h, 22 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water
2.1 Reagents: Ozone Solvents: Dichloromethane ;  -78 °C
2.2 Reagents: Triphenylphosphine ;  -78 °C → 22 °C; 4 h, 22 °C
3.1 Reagents: Potassium tert-butoxide Solvents: tert-Butanol ;  15 min, 22 °C
3.2 Reagents: Sodium bicarbonate Solvents: Water
3.3 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  1 h, 22 °C
4.1 Reagents: Hydrazine Solvents: Diethylene glycol ;  22 °C → 160 °C; 2 h, 160 °C; 160 °C → 22 °C
4.2 Reagents: Potassium hydroxide ;  22 °C → 180 °C; 4 h, 180 °C; 180 °C → 22 °C
4.3 Reagents: Hydrochloric acid Solvents: Water
5.1 Reagents: Sodium periodate ,  Ruthenium trichloride Solvents: Carbon tetrachloride ,  Acetonitrile ,  Water ;  2 h, pH 7, 22 °C
6.1 Reagents: Chloro(1-methylethyl)magnesium Solvents: Tetrahydrofuran ;  -78 °C → 0 °C; 30 min, 0 °C
6.2 Reagents: Sodium bicarbonate Solvents: Water
7.1 Reagents: Pyridine ,  Thionyl chloride Solvents: Dichloromethane ;  1 h, -78 °C
7.2 Reagents: Sodium bicarbonate Solvents: Water
8.1 Reagents: Diisobutylaluminum hydride Solvents: Tetrahydrofuran ;  1 h, -78 °C
8.2 Reagents: Hydrochloric acid Solvents: Water
9.1 Solvents: Toluene ;  22 °C → 110 °C; 22 h, 110 °C
10.1 Reagents: Butyllithium Solvents: Hexane ;  30 min, 0 °C; 0 °C → -78 °C
10.2 Solvents: Tetrahydrofuran ;  1 h, -78 °C
10.3 Reagents: Sodium bicarbonate Solvents: Water
11.1 Reagents: 2-Methyl-2-butene ,  Sodium chlorite Catalysts: 2-Azatricyclo[3.3.1.13,7]dec-2-yloxy Solvents: Acetic acid ,  Dichloromethane ,  Water ;  24 h, pH 4.6, rt
11.2 Reagents: Sodium bisulfite Solvents: Water
Reference
Total Synthesis of Taiwaniadducts B, C, and D
Deng, Jun; et al, Journal of the American Chemical Society, 2014, 136(23), 8185-8188

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1-Naphthalenecarboxylic acid,decahydro-1,4a-dimethyl-6-methylene-5-[(2E)-3-methyl-2,4-pentadienyl]-, (1R,4aR,5S,8aR)- Preparation Products

1-Naphthalenecarboxylic acid,decahydro-1,4a-dimethyl-6-methylene-5-[(2E)-3-methyl-2,4-pentadienyl]-, (1R,4aR,5S,8aR)- Related Literature

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