7417-68-7

Upstream product

• 29865-97-2 2,5-dihydroxy-4-methoxy-benzaldehyde 
• 64-19-7 acetic acid 
• 765-47-9 1,2-dimethylcyclopentene 
• 72312-08-4 2-methyl-4,4,5-trimethoxycyclohexa-2,5-dienone 
• 7782-99-2 sulphurous acid 
• 614-13-1 2-methoxy-5-methyl-1,4-benzoquinone 
• 4949-20-6 (E)-2,4-pentadien-1-ol 
• 1195-09-1 5-methyl-2-methoxyphenol 
• 7721-62-2 4,5-dimethoxy-2-methylbenzaldehyde 

Downstream Products

• 614-13-1 2-methoxy-5-methyl-1,4-benzoquinone 
• 112649-72-6 2,5-bis(2-benzyloxy-4-methoxybenzoyloxy)-4-methoxytoluene 
• 100118-34-1 2-methoxy-5-methyl-1,4-benzenediol diacetate 
• 490-64-2 asaronic acid 
• 112649-75-9 2,5-bis(2-acetoxy-4-methoxybenzoyloxy)-4-methoxybenzyl bromide 
• 112649-74-8 2,5-bis(2-acetoxy-4-methoxybenzoyloxy)-4-methoxytoluene 
• 112649-70-4 2,5-bis(2,4-dimethoxybenzoyloxy)-4-methoxybenzyl bromide 
• 112649-73-7 2,5-bis(2-hydroxy-4-methoxybenzoyloxy)-4-methoxytoluene 
• 90664-32-7 5-Hydroxy-2-(2-hydroxy-4-methoxyphenyl)-6-methoxybenzofuran 
• 97242-31-4 2,5-di(3-acetoxy-5-methoxybenzoyloxy)-4-methoxybenzyl bromide 
• 97242-32-5 5-(3-acetoxy-5-methoxybenzoyloxy)-2-(3-acetoxy-5-methoxyphenyl)-6-methoxybenzofuran 
• 67259-16-9 2-(3-hydroxy-5-methoxyphenyl)-6-methoxy-5-benzofuranol 
• 97265-24-2 2,5-di(3-acetoxy-5-methoxybenzoyloxy)-4-methoxytoluene 
• 112649-69-1 2,5-bis(2,4-dimethoxybenzoyloxy)-4-methoxytoluene 

Relevant academic research and scientific papers

Dual behavior of masked o-benzoquinones in intramolecular Diels-Alder reactions. Expedient synthesis of highly functionalized cis-decalins from 2-methoxyphenols

The potential dual behavior as dienes and dienophiles of the diene moieties of masked o-benzoquinones (MOBs) 10a-e-12a-e, generated upon oxidation of 2-methoxyphenols 1-3 with BTIB in the presence of appropriate dienols, in their intramolecular Diels-Alde

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 diastereo-meric bicyclo[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.