[(3R,4aR,6S,6aS,10S,10aR,10bS)-3-ethenyl-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-5,6,6a,8,9,10-hexahydro-2H-benzo[f]chromen-5-yl] acetate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(3R,4aR,6S,6aS,10S,10aR,10bS)-3-ethenyl-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-5,6,6a,8,9,10-hexahydro-2H-benzo[f]chromen-5-yl] acetate
• 化学式: C₂₂H₃₄O₇
• 分子量: 410.5
• InChiKey: OHCQJHSOBUTRHG-JIESHHICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

文献信息

• A process for the preparation of forskolin from 9-deoxy-forskolin and intermediates used therein
  申请人：HOECHST-ROUSSEL PHARMACEUTICALS INCORPORATED

  公开号：EP0243646A1

  公开（公告）日：1987-11-04

  A method of regioselectively and stereoselectively synthesizing forskolin (8,13-epoxy-1α,6β,7β,9α-tetrahydroxy­labd-14-en-11-one) from 9-deoxyforskolin (8,13-epoxy-­1α,6β,7β,-trihydroxylabd-14-en-11-one) with a good yield is described. In a preferred embodiment, it comprises an enol ether formation from 8,13-epoxy-1α,6β,7β-trihydroxylabd-14-­en-11-one-6,7-carbonate, oxidation of the enol ether with a suitable peroxy acid to obtain 11,12-dehydro-8,13-epoxy-11-­methoxy-1α,6β,7β,9α-tetrahydrolabd-14-ene-6,7-carbonate and hydrolysis of the latter under an acidic condition to obtain 8,13-epoxy-1α,6β,7β,9α-tetrahydroxylabd-14-en-11-one-6,7-­carbonate. As an alternative way of protecting the two hydroxy groups at carbon-6 and carbon-7, they may also be converted to dimethyl acetal during the synthetic sequence. Four compounds produced in the synthetic scheme as intermediates, namely, 9,11-dehydro-8,13-epoxy-11-methoxy-­1α,6β,7β-trihydroxy-labd-14-ene-6,7-carbonate and 11,12-­dehydro-8,13-epoxy-11-methoxy-1α,6β,7β,9α-tetrahydroxylabd-­14-ene-6,7-carbonate and the corresponding dimethyl acetal compounds are believed to be novel.

  本发明描述了一种以 9-脱氧福斯克林（8,13-环氧-1α,6β,7β,9α-三羟基赖百当-14-烯-11-酮）为原料，进行区域选择性和立体选择性合成福斯克林（8,13-环氧-1α,6β,7β,9α-四羟基赖百当-14-烯-11-酮）并获得良好收率的方法。在一个优选的实施方案中，它包括从 8,13-环氧-1α,6β,7β-三羟基赖百当-14-烯-11-酮-6,7-碳酸酯中生成烯醇醚，用合适的过氧酸氧化烯醇醚，得到 11,12-脱氢-8-环氧-11-甲氧基赖百当-14-烯-11-酮-6,7-碳酸酯、13-环氧-11-甲氧基-1α,6β,7β,9α-四氢巴豆-14-烯-6,7-碳酸酯，后者在酸性条件下水解，得到 8,13-环氧-1α,6β,7β,9α-四羟基巴豆-14-烯-11-酮-6,7-碳酸酯。作为保护碳 6 和碳 7 上两个羟基的另一种方法，也可以在合成过程中将它们转化为二甲基缩醛。在合成方案中作为中间体产生的四种化合物，即 9,11-脱氢-8,13-环氧-11-甲氧基-1α,6β,7β-三羟基-赖百当-14-烯-6,7-碳酸酯和 11,12-脱氢-8,13-环氧-11-甲氧基-1α,6β,7β,9α-四羟基-赖百当-14-烯-6,7-碳酸酯以及相应的二甲基乙缩醛化合物被认为是新颖的。
• US4902696A
  申请人：——

  公开号：US4902696A

  公开（公告）日：1990-02-20
• US5846992A
  申请人：——

  公开号：US5846992A

  公开（公告）日：1998-12-08