Facile total synthesis of the (−)-Heliconol A
- 作者：Weiguo Quan ; Binxun Yu ; Jiyong Zhang ; Qiren Liang ; Xuegong She ; Xinfu Pan
- 关键词：Marine natural products ; Molluscs ; Aplysiol ; Absolute stereochemistry
- 刊名：Tetrahedron
- 出版年：2007
- 期刊代码：107_00404020
- 类别：ch
- 出版时间：1 October 2007
- 卷：63
- 期：40
- 页码：9991-9996
- 文件大小：266 K
摘要
The facile total synthesis of the (−)-Heliconol A (ent-1) as well as its diastereoisomer 18 is described, in which different reaction sequences lead to different results. The osmylation of 15 followed by hydrolysis afforded a single isomer 18, otherwise, a mixture of ent-1 and 18 resulted. Other important processes include the catalytic asymmetric CBS reduction and induced osmylation. The synthesis proceeded with a sequence of 11 steps, affording ent-1 in 9.0%and 18 in 22%overall yield, respectively.