Synthetic Approach to the Core Structure of Oleandrin and Related Cardiac Glycosides with Highly Functionalized Ring D

被引：15

作者：

Michalak, Karol ^{[1
]}

Morawiak, Maja ^{[1
]}

Wicha, Jerzy ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, Ul Martina Kasprzaka 44-52, PL-01224 Warsaw, Poland

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 23期

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; SILYL ENOL ETHERS; NERIUM-OLEANDER; BIOACTIVE CARDENOLIDES; STEROIDS; CANCER; OUABAGENIN; OXIDATION; ALCOHOLS; ENONES;

D O I：

10.1021/acs.orglett.6b03157

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthetic approach to the core structure of cardiac glycoside oleandrin exhibiting a potent cytotoxic activity, starting from a common androstane derivative, has been accomplished. The synthesis is focused on stereoselective transformations in the densely substituted and sterically shielded five-membered ring (steroid ring D). The developed synthesis paves a route to the synthesis of related bufadienolides, i.e., constituents of traditional drug Ch'an Su, bufotalin, and cinobufagin.

引用

页码：6148 / 6151

页数：4

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