立体控制和高效全合成 (-)-stephanotic 酸甲酯和 (-)-celogentin C。

Stereocontrolled and efficient total synthesis of (-)-stephanotic acid methyl ester and (-)-celogentin C.

机构信息

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing 100191, China.

出版信息

Org Lett. 2010 Mar 5;12(5):956-9. doi: 10.1021/ol902944f.

DOI:10.1021/ol902944f

PMID:20108939

Abstract

A highly stereocontrolled and efficient total synthesis of (-)-stephanotic acid methyl ester and (-)-celogentin C was accomplished in longest linear 14 steps (4.6% overall yield) and in 20 steps (1.6% overall yield) from l-tryptophan, respectively. Highlights of the synthesis include a tandem asymmetric Michael addition/bromination/azidation strategy for a ready access to the leucine-tryptophan moiety (Leu-Trp linkage) and an oxidative coupling reaction to form the indole-imidazole linkage.

摘要

（-）-Stephanoic 酸甲酯和（-）-Celogentin C 的高度立体控制和高效全合成分别通过最长线性 14 步（总产率为 4.6%）和 20 步（总产率为 1.6%）从 l-色氨酸实现。合成的亮点包括串联不对称迈克尔加成/溴化/叠氮化策略，可轻松获得亮氨酸-色氨酸部分（Leu-Trp 键）和氧化偶联反应形成吲哚-咪唑键。