（-）-查莫布曲辛 A 的（+）-脱氢枞胺合成。

Synthesis of (-)-Chamobtusin A from (+)-Dehydroabietylamine.

机构信息

Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo , 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan.

出版信息

J Org Chem. 2016 Dec 2;81(23):11866-11870. doi: 10.1021/acs.joc.6b02328. Epub 2016 Nov 7.

DOI:10.1021/acs.joc.6b02328

PMID:27768308

Abstract

Chamobtusin A, a unique diterpene alkaloid isolated from Chamaecyparis obtusa cv. tetragon, is considered to be biosynthesized from an abietane diterpenoid. On the basis of this biosynthetic hypothesis, ferruginol (15) was synthesized from (+)-dehydroabietylamine and then biomimetically transformed into (-)-chamobtusin A in 6 steps (12 steps from (+)-dehydroabietylamine).

摘要

从柏科圆柏变种四棱杉中分离得到的独特二萜生物碱察布亭 A，被认为是由枞烷二萜生物合成的。根据这一生物合成假说，从（+）-脱氢枞胺合成了铁屎米醇（15），然后通过仿生转化在 6 步（从（+）-脱氢枞胺 12 步）中转化为（-）-察布亭 A。