（±）-γ-柔红霉素的汇聚全合成。

A convergent total synthesis of (±)-γ-rubromycin.

机构信息

Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106-9510, USA.

出版信息

J Am Chem Soc. 2011 Apr 27;133(16):6114-7. doi: 10.1021/ja1115524. Epub 2011 Mar 31.

Abstract

An expeditious convergent total synthesis affords (±)-γ-rubromycin (1) in 4.4% overall yield. The longest linear sequence is 12 steps from commercial starting materials. The effort highlights a remarkable late-stage oxidative [3 + 2] cycloaddition for construction of the spiroketal, a regioselective carbonyl methylenation, a boron tribromide promoted deprotection, ortho- to para- naphthoquinone spiroketal rearrangement, and a tautomerization sequence.

摘要

一种快速收敛的总合成方法以 4.4%的总收率提供（±）-γ-柔红霉素（1）。最长的线性序列从商业起始原料开始有 12 步。该方法的突出特点是在构建螺环缩酮时采用了显著的晚期氧化[3+2]环加成反应、区域选择性羰基亚甲基化反应、三溴化硼促进的脱保护反应、邻-对-萘醌螺环缩酮重排反应和互变异构化反应序列。