72312-07-3Relevant articles and documents
INTRODUCTION OF A HYDROXYL GROUP INTO THE CREOSOL MOLECULE
Kozlova, I. V.,Obol'nikova, E. A.,Chupina, L. N.,Bekker, A. R.,Samokhvalov, G. I.
, p. 296 - 299 (2007/10/02)
The introduction of a hydroxyl group into the molecule of 2-methoxy-4-methylphenol through Rieche formylation and Baeyer-Villiger oxidation was investigated.With dichloromethyl methyl ether meta-formylation of creosol occurs.
A SYNTHESIS OF GYMNOMITROL
Buechi, George,Chu, Ping-Sun
, p. 4509 - 4514 (2007/10/02)
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
Büchi, George,Chu, Ping-Sun
, p. 4509 - 4513 (2014/12/10)
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.
A synthesis of gymnomitrol
Bchi, George,Chu, Ping-Sun
, p. 4509 - 4513 (2015/01/08)
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.