Cas no 865-21-4 (vinblastine)

vinblastine structure
vinblastine structure
Product Name:vinblastine
CAS No:865-21-4
MF:C46H58N4O9
MW:810.974133014679
MDL:MFCD05662370
CID:40076
PubChem ID:3823887
Update Time:2024-10-26

vinblastine Chemical and Physical Properties

Names and Identifiers

    • vinblastine
    • VINBLASTINE SULFATE(RG)
    • [3aR-[3aa,4b,5b,5ab,9(3R*,5S*,7R*,9S*),10bR*,13aa]]-Methyl 4-(acetyloxy)-3a-ethyl-9-[5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino[5,4-b]indol-9-yl]-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-1H-indolizino[8,1-cd]carbazole-5-carboxylate
    • 1H-Indolizino[8,1-cd]carbazole, vincaleukoblastine deriv.
    • 1H-Indolizino[8,1-cd]carbazole-5-carboxylic acid, 4-(acetyloxy)-3a-ethyl-9-[5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino[5,4-b]indol-9-yl]-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-, methyl ester, [3aR-[3aa,4b,5b,5ab,9(3R*,5S*,7R*,9S*),10bR*,13aa]]-
    • 2H-3,7-Methanoazacycloundecino[5,4-b]indole, vincaleukoblastine deriv.
    • Rozevin
    • C46H58N4O9
    • Vinblastine-d3
    • Vinblastine-d6 Sulfate
    • vinblastine sulfuric acid salt
    • Vinblastine sulphate
    • Vinblastine,Vincaleukoblastine
    • Vincaleucoblastin
    • Vincaleucoblastine
    • Vincaleukoblastine
    • Vincoblastine
    • 1H-Indolizino[8,1-cd]carbazole, vincaleukoblastine deriv. (ZCI)
    • 2H-3,7-Methanoazacycloundecino[5,4-b]indole, vincaleukoblastine deriv. (ZCI)
    • Vinblastine (7CI)
    • (+)-Vinblastine
    • 1H-Indolizino[8,1-cd]carbazole-5-carboxylic acid, 4-(acetyloxy)-3a-ethyl-9-[5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino[5,4-b]indol-9-yl]-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-, methyl ester, [3aR-[3aα,4β,5β,5aβ,9(3R*,5S*,7R*,9S*),10bR*,13aα]]-
    • [3aR-[3aα,4β,5β,5aβ,9(3R*,5S*,7R*,9S*),10bR*,13aα]]-Methyl 4-(acetyloxy)-3a-ethyl-9-[5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino[5,4-b]indol-9-yl]-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-1H-indolizino[8,1-cd]carbazole-5-carboxylate
    • Dimethyl(2β,3β,4β,5α,12β,19α)-15-[(5S,9S)-5-ethyl-5-hydroxy-9-(methoxycarbonyl)-1,4,5,6,7,8,9,10-octahydro-2H-3,7-methanoazacycloundecino[5,4-b]indol-9-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3,4-dicarboxylate
    • MeSH ID: D014747
    • Valban
    • Vinblastin
    • VLB
    • methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraene-10-carboxylate
    • Vinblastina (TN)
    • CHEBI:27375
    • 132142-72-4
    • Q-100868
    • AKOS015969678
    • HMS2090K05
    • NS00003095
    • AB01273959-02
    • NCGC00181127-02
    • CHEMBL22969
    • 865-21-4
    • Q282629
    • SCHEMBL17813675
    • Vinblastine (Vincaleucoblastine)
    • methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5(10),6,8-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraene-10-carboxylate
    • methyl acetoxy-ethyl-(ethyl-hydroxy-methoxycarbonyl-[?]yl)-hydroxy-methoxy-methyl-[?]carboxylate
    • Vinblastine (INN)
    • BDBM227643
    • NCGC00263548-07
    • EN300-130971
    • AB01273959-01
    • NCGC00181127-01
    • C07201
    • SCHEMBL6146
    • D08675
    • DTXSID8021430
    • NCI60_004200
    • 72401-36-6
    • VINDESINE SULFATE IMPURITY B [EP IMPURITY]
    • NSC816570
    • NCI-C04842
    • methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5(10),6,8-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraene-10-carboxylate
    • Velban
    • Vinblastinum [INN-Latin]
    • CCRIS 9002
    • VINBLASTINE [WHO-DD]
    • VINCRISTINE SULFATE IMPURITY H [EP IMPURITY]
    • NSC 47842
    • BRD-K01188359-001-02-0
    • CHEMBL159
    • NSC-816570
    • DB00570
    • HY-17418
    • Vinblastina [DCIT]
    • AS-15821
    • BSPBio_001228
    • BRD-K01188359-065-02-5
    • EINECS 212-734-0
    • (2alpha,2'beta,3alpha,5beta,19beta)-vincaleukoblastine
    • L01CA01
    • SCHEMBL3628
    • 1z2b
    • (3AR-(3AALPHA,4BETA,5BETA,5ABETA,9(3R*,5S*,7R*,9S*),10BR*,13AALPHA))-METHYL 4-(ACETYLOXY)-3A-ETHYL-9-(5-ETHYL-1,4,5,6,7,8,9,10-OCTAHYDRO-5-HYDROXY-9- (METHOXYCARBONYL)-2H-3,7-METHANOAZACYCLOUNDECINO(5,4-B)INDOL-9-YL)- 3A,4,5,5A,6,11,12,13A-OCTAHYDRO-5-HYDROXY-8-METHOXY-6-METHYL-1H-INDOLIZINO (8,1-CD)CARBAZOLE-5-CARBOXYLATE
    • 1H-Indolizino(8,1-cd)carbazole-5-carboxylic acid, 4-(acetyloxy)-3a-ethyl-9-(5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino(5,4-b)indol-9-yl)-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-, methyl ester, (3aR-(3aalpha,4beta,5beta,5abeta,9(3R*,5S*,7R*,9S*),10bR*,13aalpha))-
    • methyl (3aR,3a1R,4R,5S,5aR,10bR)-4-acetoxy-3a-ethyl-9-((5S,7R,9S)-5-ethyl-5-hydroxy-9-(methoxycarbonyl)-1,4,5,6,7,8,9,10-octahydro-2H-3,7-methano[1]azacycloundecino[5,4-b]indol-9-yl)-5-hydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate
    • VINBLASTINE [INN]
    • UNII-5V9KLZ54CY
    • VINBLASTINE [MI]
    • BIDD:PXR0201
    • NSC 49842
    • BDBM50012278
    • (2ALPHA,2''''BETA,3BETA,4ALPHA,5BETA)-VINCALEUKOBLASTINE
    • methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
    • [3H]-Vinblastine
    • CS-1336
    • VINBLASTINE [VANDF]
    • VINBLASTINE [HSDB]
    • NCGC00485975-02
    • NSC-47842
    • Vinblastinum (INN-Latin)
    • NCGC00022585-04
    • EN300-19874057
    • Vinblastinum
    • Vinblastina
    • VR-8
    • 5V9KLZ54CY
    • (2ALPHA,2'BETA,3BETA,4ALPHA,5BETA)-VINCALEUKOBLASTINE
    • DTXCID801430
    • Vinblastine [INN:BAN]
    • NDC 0002-1452-01
    • GTPL6851
    • cid_5388983
    • JXLYSJRDGCGARV-CFWMRBGOSA-N
    • Nincaluicolflastine
    • NCGC00022585-05
    • AC-24191
    • VBL
    • (3aR-(3aalpha,4beta,5beta,5abeta,9(3R*,5S*,7R*,9S*),10bR*,13aalpha))-methyl 4-(acetyloxy)-3a-ethyl-9-(5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino(5,4-b)indol-9-yl)-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-1H-indolizino(8,1-cd)carbazole-5-carboxylate
    • HSDB 3263
    • AKOS015965500
    • JXLYSJRDGCGARV-UHFFFAOYSA-N
    • CHEBI:125454
    • LSM-36946
    • CHEMBL4788494
    • BRD-A85648045-001-01-6
    • Vinrosidine
    • 15228-71-4
    • AKOS040894271
    • Neuro_000020
    • Q27216072
    • Leurosidine
    • VinblastineVincaleukoblastine; Vinblastina
    • BRD-K01188359-001-03-8
    • BRD-K01188359-065-23-1
    • 1ST15295
    • MDL： MFCD05662370
    • Inchi： 1S/C46H58N4O9/c1-8-42(54)23-28-24-45(40(52)57-6,36-30(15-19-49(25-28)26-42)29-13-10-11-14-33(29)47-36)32-21-31-34(22-35(32)56-5)48(4)38-44(31)17-20-50-18-12-16-43(9-2,37(44)50)39(59-27(3)51)46(38,55)41(53)58-7/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3/t28-,37-,38+,39+,42-,43+,44+,45-,46-/m0/s1
    • InChI Key： JXLYSJRDGCGARV-CFWMRBGOSA-N
    • SMILES： C([C@@]12C=CCN3[C@@H]1[C@]1(C4C=C([C@]5(C[C@@H]6C[C@@](C[N@](C6)CCC6C7C=CC=CC=7NC5=6)(O)CC)C(=O)OC)C(=CC=4N(C)[C@H]1[C@@]([C@@H]2OC(=O)C)(O)C(=O)OC)OC)CC3)C

Computed Properties

  • Exact Mass: 810.42000
  • Monoisotopic Mass: 810.42
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 12
  • Heavy Atom Count: 59
  • Rotatable Bond Count: 10
  • Complexity: 1700
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 8
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Molecular Weight: 811.0
  • XLogP3: 3.7
  • Topological Polar Surface Area: 154A^2

Experimental Properties

  • Color/Form: Powder
  • Density: 1.1325 (rough estimate)
  • Melting Point: 211-216°C
  • Boiling Point: 755.65°C (rough estimate)
  • Flash Point: No data available
  • Refractive Index: 1.6000 (estimate)
  • Solubility: ODORLESS & HYGROSCOPIC; WHITE TO SLIGHTLY YELLOW, AMORPHOUS OR CRYSTALLINE POWDER; FREELY SOL IN WATER /VINBLASTINE SULFATE/
  • PSA: 154.10000
  • LogP: 3.93170
  • Vapor Pressure: 1.03X10-27 mm Hg at 25 °C (est)
  • pka: 5.4, 7.4(at 25℃)
  • Specific Rotation: -32° (c=0.88, MeOH)

vinblastine Security Information

vinblastine Pricemore >>

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vinblastine Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
Reference
Nonoxidative coupling methodology for the synthesis of the antitumor bisindole alkaloid vinblastine and a lower-half analog: solvent effect on the stereochemistry of the crucial C-15/C-18' bond
Magnus, Philip; et al, Journal of the American Chemical Society, 1992, 114(26), 10232-45

Production Method 2

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  45 min, rt
Reference
Synthesis of (+)-Vinblastine and Its Analogues
Miyazaki, Tohru; et al, Organic Letters, 2007, 9(23), 4737-4740

Production Method 3

Reaction Conditions
1.1 Reagents: Sodium bicarbonate Solvents: Isopropanol ,  Water ;  rt
Reference
Stereocontrolled total synthesis of (+)-vinblastine
Yokoshima, Satoshi; et al, Pure and Applied Chemistry, 2003, 75(1), 29-38

Production Method 4

Reaction Conditions
1.1 Reagents: 2-Mercaptoethanol ,  1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Acetone
1.2 Reagents: Sodium bicarbonate Solvents: Isopropanol ,  Water
Reference
Stereocontrolled total synthesis of (+)-vinblastine
Yokoshima, Satoshi; et al, Journal of the American Chemical Society, 2002, 124(10), 2137-2139

Production Method 5

Reaction Conditions
1.1 Reagents: Hydrochloric acid ,  Iron chloride (FeCl3) Solvents: 2,2,2-Trifluoroethanol ,  Water ;  2 h, 23 °C
1.2 Reagents: Ferric oxalate Solvents: Water ;  23 °C → 0 °C
1.3 Reagents: Oxygen ;  20 min, 0 °C
1.4 Reagents: Sodium borohydride Solvents: Water ;  30 min, 0 °C
1.5 Reagents: Ammonium hydroxide Solvents: Water
Reference
Enantioselective synthesis of Iboga alkaloids and vinblastine via rearrangements of quaternary ammoniums
Zhang, Yun; et al, Chemical Science, 2016, 7(8), 5530-5536

Production Method 6

Reaction Conditions
1.1 Reagents: Citric acid ,  Hydrochloric acid ,  Sodium hypochlorite ,  Hydrogen peroxide ,  Sodium borohydride Solvents: Methanol ,  Dichloromethane ,  Water ;  pH 2.2; 4.5 h, pH 2.2 → pH 8.3, -5 - 0 °C
Reference
A simplified procedure for indole alkaloid extraction from Catharanthus roseus combined with a semi-synthetic production process for vinblastine
Verma, Arvind; et al, Molecules, 2007, 12(7), 1307-1315

Production Method 7

Reaction Conditions
1.1 Reagents: Maleic acid ,  Ammonium oxalate monohydrate ,  Ammonia ,  Ferric chloride hexahydrate Solvents: Water ;  0 °C; 2 h, 0 °C
1.2 Reagents: Sodium borohydride Solvents: Water ;  30 min, rt
Reference
Study on synthesis of vinblastine from catharanthine and vindoline isolated from Cantharanthus roseus
Nguyen, Le Tuan; et al, Tap Chi Hoa Hoc, 2012, 50(2), 211-215

Production Method 8

Reaction Conditions
Reference
Synthesis of the antitumor bisindole alkaloid vinblastine: diastereoselectivity and solvent effect on the stereochemistry of the crucial C-15-C-18' bond
Magnus, Philip; et al, Journal of the American Chemical Society, 1990, 112(22), 8210-12

Production Method 9

Reaction Conditions
1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran
2.1 Solvents: Methanol
2.2 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
Reference
Enantioselective syntheses of vinblastine, leurosidine, vincovaline and 20'-epi-vincovaline
Kuehne, Martin E.; et al, Journal of Organic Chemistry, 1991, 56(2), 513-28

Production Method 10

Reaction Conditions
1.1 Reagents: 2,6-Di-tert-butyl-4-methylpyridine Solvents: Nitromethane
2.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran
3.1 Reagents: Triethylamine ,  Sulfur trioxide-pyridine complex Solvents: Dimethyl sulfoxide
4.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
Reference
Nonoxidative coupling methodology for the synthesis of the antitumor bisindole alkaloid vinblastine and a lower-half analog: solvent effect on the stereochemistry of the crucial C-15/C-18' bond
Magnus, Philip; et al, Journal of the American Chemical Society, 1992, 114(26), 10232-45

Production Method 11

Reaction Conditions
1.1 Reagents: Ferric oxalate ,  Oxygen Solvents: Water ;  10 min, 0 °C
1.2 Reagents: Hydrochloric acid ,  Sodium borohydride Solvents: 2,2,2-Trifluoroethanol ,  Water ;  30 min, 0 °C
1.3 Reagents: Ammonium hydroxide Solvents: Water
Reference
10'-Fluorovinblastine and 10'-Fluorovincristine: Synthesis of a Key Series of Modified Vinca Alkaloids
Gotoh, Hiroaki; et al, ACS Medicinal Chemistry Letters, 2011, 2(12), 948-952

Production Method 12

Reaction Conditions
1.1 Solvents: Methanol
1.2 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
Reference
Enantioselective syntheses of vinblastine, leurosidine, vincovaline and 20'-epi-vincovaline
Kuehne, Martin E.; et al, Journal of Organic Chemistry, 1991, 56(2), 513-28

Production Method 13

Reaction Conditions
1.1 Reagents: Sodium bicarbonate Solvents: Acetone ,  Water ;  rt
Reference
Total synthesis of (+)-vinblastine
Yokoshima, Satoshi; et al, Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 2001, 43, 163-168

Production Method 14

Reaction Conditions
1.1 Reagents: 2-Mercaptoethanol ,  1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Acetonitrile ;  rt
2.1 Reagents: Sodium bicarbonate Solvents: Acetone ,  Water ;  rt
Reference
Total synthesis of (+)-vinblastine
Yokoshima, Satoshi; et al, Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 2001, 43, 163-168

Production Method 15

Reaction Conditions
1.1 Reagents: Triethylamine Solvents: Methanol
1.2 Reagents: 2-Mercaptoethanol ,  1,8-Diazabicyclo[5.4.0]undec-7-ene
1.3 Reagents: Sodium bicarbonate Solvents: Isopropanol
Reference
First de novo synthesis of the bisindole alkaloid vinblastine
Schneider, Christoph, Angewandte Chemie, 2002, 41(22), 4217-4219

Production Method 16

Reaction Conditions
1.1 Reagents: Triethylamine Solvents: Methanol
1.2 Reagents: 2-Mercaptoethanol ,  1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Acetone
2.1 Reagents: Sodium bicarbonate Solvents: Isopropanol ,  Water ;  rt
Reference
Stereocontrolled total synthesis of (+)-vinblastine
Yokoshima, Satoshi; et al, Pure and Applied Chemistry, 2003, 75(1), 29-38

Production Method 17

Reaction Conditions
1.1 Reagents: Hydrochloric acid Solvents: Water
Reference
Photochemical one-pot synthesis of vinblastine and vincristine
Pennanen, S.; et al, Photochemistry and Photobiology, 1990, 51(5), 515-18

Production Method 18

Reaction Conditions
1.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran
2.1 Reagents: Triethylamine ,  Sulfur trioxide-pyridine complex Solvents: Dimethyl sulfoxide
3.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
Reference
Nonoxidative coupling methodology for the synthesis of the antitumor bisindole alkaloid vinblastine and a lower-half analog: solvent effect on the stereochemistry of the crucial C-15/C-18' bond
Magnus, Philip; et al, Journal of the American Chemical Society, 1992, 114(26), 10232-45

Production Method 19

Reaction Conditions
1.1 Reagents: 2,6-Di-tert-butyl-4-methylpyridine Solvents: Nitromethane
2.1 -
Reference
Synthesis of the antitumor bisindole alkaloid vinblastine: diastereoselectivity and solvent effect on the stereochemistry of the crucial C-15-C-18' bond
Magnus, Philip; et al, Journal of the American Chemical Society, 1990, 112(22), 8210-12

Production Method 20

Reaction Conditions
1.1 Reagents: Triethylamine ,  Sulfur trioxide-pyridine complex Solvents: Dimethyl sulfoxide
2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
Reference
Nonoxidative coupling methodology for the synthesis of the antitumor bisindole alkaloid vinblastine and a lower-half analog: solvent effect on the stereochemistry of the crucial C-15/C-18' bond
Magnus, Philip; et al, Journal of the American Chemical Society, 1992, 114(26), 10232-45

Production Method 21

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ;  1 h, rt
1.2 Solvents: Tetrahydrofuran ;  2 h, rt
1.3 Solvents: Water ;  rt
2.1 Reagents: Hydrochloric acid ,  Iron chloride (FeCl3) Solvents: 2,2,2-Trifluoroethanol ,  Water ;  2 h, 23 °C
2.2 Reagents: Ferric oxalate Solvents: Water ;  23 °C → 0 °C
2.3 Reagents: Oxygen ;  20 min, 0 °C
2.4 Reagents: Sodium borohydride Solvents: Water ;  30 min, 0 °C
2.5 Reagents: Ammonium hydroxide Solvents: Water
Reference
Enantioselective synthesis of Iboga alkaloids and vinblastine via rearrangements of quaternary ammoniums
Zhang, Yun; et al, Chemical Science, 2016, 7(8), 5530-5536

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