Synthetic Approach to Wortmannilactone C

被引：15

作者：

Brandt, Damien ^{[1
]}

Dittoo, Aurelia ^{[1
]}

Bellosta, Veronique ^{[1
]}

Cossy, Janine ^{[1
]}

机构：

[1] PSL Res Univ, Inst Chem Biol & Innovat CBI, Lab Chim Organ, UMR 8231,ESPCI ParisTech,CNRS, F-75231 Paris 05, France

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 04期

关键词：

ABSOLUTE-CONFIGURATION; LEUCASCANDROLIDE-A; O-METHYLMANDELATE; CARBOXYLIC-ACIDS; MACROLIDES; ALCOHOLS; FRAGMENT; ESTER; CORE;

D O I：

10.1021/ol5036112

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A diastereomer of wortmannilactone C has been synthesized according to a convergent and versatile strategy from tert-butyl 3-hydroxypropanoate and ethyl (R)-3-hydroxybutanoate. The key steps are a Liebeskind cross-coupling and a Horner-Wadsworth-Emmons (HWE) reaction to construct the macrolactone. The stereogenic centers at C9, C11, and C21 were controlled by enantioselective allyltitanations, and the C19 stereocenter was controlled by using a Noyori reduction of an acetylenic ketone.

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页码：816 / 819

页数：4

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