作为血小板聚集抑制剂的半日花烷二萜类化合物与贝壳杉烯二醇相关的合成

Synthesis of manool-related labdane diterpenes as platelet aggregation inhibitors.

作者信息

Yasui K, Kawada K, Kagawa K, Tokura K, Kitadokoro K, Ikenishi Y

机构信息

Shionogi Research Laboratories, Shionogi & Co., Ltd., Osaka, Japan.

出版信息

Chem Pharm Bull (Tokyo). 1993 Oct;41(10):1698-707. doi: 10.1248/cpb.41.1698.

DOI:10.1248/cpb.41.1698

PMID:8281569

Abstract

Enantioselective total synthesis of the labdane diterpene (-)-1, was achieved starting from the R-(-)-enantiomer of the Wieland-Miescher ketone. The enantiomer (+)-1 was obtained by partial synthesis via microbial transformation of sclareol. These results established that the natural compound (+)-1, a platelet aggregation inhibitor, has a normal absolute stereochemistry like that of manool. The B-norlabdane-related compound 44 was also synthesized using a novel ring contraction reaction.

摘要

从维兰德-米舍尔酮的R-(-)-对映体出发，实现了对映选择性全合成拉丹烷二萜(-)-1。对映体(+)-1通过对香紫苏醇的微生物转化进行部分合成得到。这些结果表明，天然化合物(+)-1，一种血小板聚集抑制剂，具有与马尼醇类似的正常绝对立体化学结构。还使用一种新型的环收缩反应合成了与B-降拉丹烷相关的化合物44。