71564-38-0

Upstream product

• 39863-74-6 gymnomitrone 
• 72312-11-9 (3aS,4R,6S,8S,8aS,9R)-6-Methoxy-3a,8,8a-trimethyl-9-(tetrahydro-pyran-2-yloxy)-octahydro-4,8-methano-azulen-5-one 
• 765-47-9 1,2-dimethylcyclopentene 
• 72312-08-4 2-methyl-4,4,5-trimethoxycyclohexa-2,5-dienone 
• 7721-62-2 4,5-dimethoxy-2-methylbenzaldehyde 
• 1120-72-5 2-Methylcyclopentanone 
• 10472-24-9 methyl 2-oxocyclopentane-1-carboxylate 
• 72312-07-3 2-hydroxy-4,5-dimethoxytoluene 
• 72312-09-5 (4S,8R,9S)-9-Hydroxy-6-methoxy-3a,8,8a-trimethyl-2,3,3a,4,8,8a-hexahydro-1H-4,8-methano-azulen-5-one 
• 72312-10-8 (3aα,4α,6β,8α,8aα,9R^*)-octahydro-9-hydroxy-6-methoxy-3a,8,8a-trimethyl-4,8-methanoazulen-5(1H)-one 
• 72312-13-1 (3aα,4α,8α,8aα,9R^*)-octahydro-3a,8,8a-trimethyl-9-<(tetrahydro-2H-pyran-2-yl)oxy>-4,8-methanoazulen-5(1H)-one 
• 72312-12-0 2-((3aR,4R,8S,8aR,9S)-3a,4,8a-Trimethyl-7-methylene-decahydro-4,8-methano-azulen-9-yloxy)-tetrahydro-pyran 

Relevant academic research and scientific papers

Gymnomitrane-type sesquiterpenes of the liverworts Gymnomitrion obtusum and Reboulia hemisphaerica

The sesquiterpene constituents of the liverworts Gymnomitrion obtusum Lindb. and Reboulia hemisphaerica (L.) Raddi were investigated. In addition to many known compounds, a new sesquiterpene hydrocarbon, (-)-gymnomitra- 3(15),4-diene was isolated and identified. Gymnomitrone, a sesquiterpene ketone, was found in nature for the first time.

A SYNTHESIS OF GYMNOMITROL

Condensation of 1,2-dimethylcyclopentene 10 with 2-methyl-4,4,5-trimethoxycyclohexa-2,5-dienone 7 in methylene chloride-nitromethane with added stannic chloride gave a mixture of the two diastereomeric bicyclooctanes 13 and 14 by ionic cycloaddition.After selective reduction of the saturated carbonyl group with sodium borohydride, and hydrogenation of the double bond the two epimers 18 and 20 (ratio 3.3:1) were separable by chromatography.Protection of the hydroxy group in 18 with dihydropyran and, reduction of the α-methoxyketone 19 with calcium in liquid ammonia gave ketone 21.Gymnomitrol 1 was then prepared by Wittig olefination followed by deprotection of the hydroxy group.

A synthesis of gymnomitrol

Condensation of 1,2 - dimethylcyclopentene 10 with 2 - methyl - 4,4, 5 - trimethoxycyclohexa - 2,5 -dienone 7 in methylene chloride - nitromethane with added stannic chloride gave a mixture of the two diastereomeric bicycle[3.2.1]octanes 13 and 14 by ionic [4+2]cycloaddition. After selective reduction of the saturated carbonyl group with sodium borohydride, and hydrogenation of the double bond the two epimers 18 and 20 (ratio 3.3:1) were separable by chromatography. Protection of the hydroxy group in 18 with dihydropyran and, reduction of the α-methoxyketone 19 with calcium in liquid ammonia gave ketone 21. Gymnomitrol 1 was then prepared by Wittig olefination followed by deprotection of the hydroxy group.