An efficient synthesis of lactacystin β-lactone

被引：60

作者：

Donohoe, TJ

Sintim, H

Sisangia, L

Harling, JD

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

[2] GlaxoSmithKline, Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 17期

关键词：

aldol reaction; heterocycles; natural products; reduction; total synthesis;

D O I：

10.1002/anie.200453843

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A key step in the synthesis of lactacystin β-lactone (3), an inhibitor of the 20 S proteasome, was the ammonia-free reductive aldol reaction of pyrrole 1 to form 2 with complete anti selectivity. This route to 3 takes just 13 steps (14% overall yield) and allows the late-stage stereoselective introduction of a methyl group at C4, which is crucial for the production of analogues. Boc = tert-butoxycarbonyl.

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页码：2293 / 2296

页数：4

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