Production Method 1

96405-62-8

Reaction Conditions

1.1 Reagents: Acetic acid Solvents: Water

Reference

Enantiospecific Syntheses of (+)-Goniofufurone, (+)-7-epi-Goniofufurone, (+)-Goniobutenolide A, (-)-Goniobutenolide B, (+)-Goniopypyrone, (+)-Altholactone, (+)-Goniotriol, and (+)-7-Acetylgoniotriol

Shing, Tony K. M.; Tsui, Hon-Chung; Zhou, Zhao-Hui, Journal of Organic Chemistry, 1995, 60(10), 3121-30

Production Method 2

96405-62-8

Reaction Conditions

1.1 Reagents: Pyridine, hydrofluoride (1:1) Solvents: Acetonitrile ;  2 d, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt
1.3 Reagents: Titanium tetrachloride Solvents: Dichloromethane ;  2 h, rt
1.4 Reagents: Sodium bicarbonate Solvents: Water ;  rt

Reference

Stereoselective synthesis of (+)-goniodiol, (+)-goniotriol, (-)-goniofupyrone, and (+)-altholactone using a catalytic asymmetric hetero-Diels-Alder/allylboration approach

Favre, Annaick; Carreaux, Francois; Deligny, Michael; Carboni, Bertrand, European Journal of Organic Chemistry, 2008, (29), 4900-4907

Production Method 3

96405-62-8

Reaction Conditions

Reference

Julia-Colonna asymmetric epoxidation of furyl styryl ketone as a route to intermediates to naturally-occurring styryl lactones

Chen, Wei-Ping; Roberts, Stanley M., Journal of the Chemical Society, 1999, (2), 103-105

Production Method 4

96405-62-8

Reaction Conditions

Reference

Concise syntheses of novel styryl lactones, (+)-goniofufurone, (+)-goniopypyrone, (+)-goniotriol, (+)-8-acetylgoniotriol, and (+)-altholactone

Tsubuki, Masayoshi; Kanai, Kazuo; Honda, Toshio, Synlett, 1993, (9), 653-5

Production Method 5

162600-03-5

96405-62-8

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid Solvents: Tetrahydrofuran ,  Water

Reference

Asymmetric total synthesis of (+)-goniotriol and (+)-goniofufurone

Yang, Zhi-cai; Zhou, Wei-shan, Tetrahedron, 1995, 51(5), 1429-36

Production Method 6

153619-50-2

96405-62-8

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane

Reference

Stereocontrolled syntheses of novel styryl lactones, (+)-goniodiol, (+)-goniotriol, (+)-8-acetylgoniotriol, (+)-goniofufurone, (+)-9-deoxygoniopypyrone, (+)-goniopypyrone, and (+)-altholactone from common intermediates and cytotoxicity of their congeners

Tsubuki, Masayoshi; Kanai, Kazuo; Nagase, Hiromasa; Honda, Toshio, Tetrahedron, 1999, 55(9), 2493-2514

Production Method 7

96405-62-8

Reaction Conditions

1.1 Reagents: Titanium tetrachloride Solvents: Dichloromethane ;  0 °C; 1.5 h, 0 °C → rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt

Reference

Stereoselective Total Synthesis of Bioactive Styryllactones (+)-Goniofufurone, (+)7-epi-Goniofufurone, (+)-Goniopypyrone, (+)-Goniotriol, (+)-Altholactone, and (-)-Etharvensin

Prasad, Kavirayani R.; Gholap, Shivajirao L., Journal of Organic Chemistry, 2008, 73(1), 2-11

Production Method 8

96405-62-8

Reaction Conditions

1.1 Reagents: Titanium tetrachloride Solvents: Dichloromethane ;  0 °C; 2 h, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  0 °C

Reference

Synthesis of (+)-goniopypyrone and (+)-goniotriol using Pd-catalyzed carbonylation

Miyazawa, Yuki; Sugimoto, Makoto; Tanaka-Oda, Ayumi; Makabe, Hidefumi, Tetrahedron Letters, 2019, 60(36),

Production Method 9

96405-62-8

Reaction Conditions

Reference

Total synthesis of antitumor Goniothalamus styryllactones

Surivet, Jean-Philippe; Vatele, Jean-Michel, Tetrahedron, 1999, 55(45), 13011-13028

Production Method 10

96405-62-8

Reaction Conditions

Reference

Stereoselective Syntheses of (+)-Goniotriol, (+)-8-Acetylgoniotriol, (+)-Goniodiol, (+)-9-Deoxygoniopypyrone, (+)-Altholactone, and (-)-Goniofupyrone

Mukai, Chisato; Hirai, Syuichi; Hanaoka, Miyoji, Journal of Organic Chemistry, 1997, 62(19), 6619-6626

Production Method 11

96405-62-8

Reaction Conditions

Reference

Total synthesis of (-)-goniopypyrone

Zhou, Zhaohui; Shing, Tony K.M., Chinese Journal of Chemistry, 1993, 11(5), 479-80

Goniotriol Raw materials

• 2H-Pyran-3(6H)-one, 2-(2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)-6-hydroxy-, [2S-[2α(4S*,5S*),6α]]-
• D-xylo-Hept-2-enonic acid, 2,3-dideoxy-4,6-bis-O-(methoxymethyl)-7-C-phenyl-, δ-lactone, (7R)-

Goniotriol Preparation Products

• Goniotriol (96405-62-8)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrans Dihydropyranones
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrans Pyranones and derivatives Dihydropyranones
• Solvents and Organic Chemicals Organic Compounds Alcohol/Ether

• 96422-53-6(2H-Pyran-2-one,6-[(1R,2R)-1-(acetyloxy)-2-hydroxy-2-phenylethyl]-5,6-dihydro-, (6R)-)
• 96422-52-5(Goniodiol)
• 136778-40-0(Goniodiol diacetate)
• 144429-71-0(2H-Pyran-2-one, 6-[2-(acetyloxy)-1-hydroxy-2-phenylethyl]-5,6-dihydro-,[6R*(1S*,2R*)]-)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)