Tetrahedron p. 4509 - 4514 (1981)
Update date:2022-07-29
Topics:
Buechi, George
Chu, Ping-Sun
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 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.
View MoreSuzhou SuKaiLu Chemical Technology Co., Ltd.
Contact:+86-512-62766020
Address:Floor 4, Building 1, Xinyi Pharmaceutical Valley Wisdom Industrial Park, 415 Changyang Street, Suzhou Industrial Park, Jiangsu Province
Contact:+86 180 6092 1829
Address:102-31, No. 1 Bldg, No. 1888, HongXiang West Road, XiangAn
Contact:+86-158-5814-5714
Address:No.9 YanAn Road,Hangzhou,Zhejiang,China
YanCheng LongShen Chemical Co.,Ltd.
Contact:+86-515-86668866
Address:No.13,Weiyi Road,Funing Aoyang Industrial Park
Nanjing Chemzam Pharmtech Co., Ltd.
Contact:+86-25-86462165,+86-13915979898
Address:C5-1，6 Maiyue Road，Maigaoqiao，Nanjing，Jiangsu，China
Doi:10.1002/adsc.200700425
(2008)Doi:10.1021/ja00383a045
(1982)Doi:10.1016/S0040-4020(98)00646-2
(1998)Doi:10.1016/j.bioorg.2021.104969
(2021)Doi:10.1021/ja01020a047
(1968)Doi:10.1016/j.molstruc.2013.05.010
(2013)
