采用临时硅连接的RCM策略对(+)-链唑啉进行立体选择性全合成。

Stereoselective total synthesis of (+)-streptazolin by using a temporary silicon-tethered RCM strategy.

作者信息

Li Fangzheng, Miller Marvin J

机构信息

Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA.

出版信息

J Org Chem. 2006 Jul 7;71(14):5221-7. doi: 10.1021/jo060555y.

DOI:10.1021/jo060555y

PMID:16808509

Abstract

A stereoselective total synthesis of (+)-streptazolin 1 was accomplished starting from readily available aminocyclopentenol (-)-7. The synthetic sequence highlights an intramolecular aldol condensation strategy to construct the piperidine core and a silicon-tethered ring-closing metathesis strategy to install the Z exocyclic ethylidene side chain of streptazolin. Separate protodesilylation and Tamao oxidation of a common intermediate 32 afforded streptazolin and the precursor for 13-hydroxystreptazolin. The overall yield for (+)-streptazolin 1 from aminocyclopentenol (-)-7 was 4.8% for a total of 16 steps.

摘要

从容易获得的氨基环戊烯醇（-）-7出发，完成了（+）-链唑啉1的立体选择性全合成。合成路线突出了用于构建哌啶核心的分子内羟醛缩合策略以及用于安装链唑啉的Z型环外亚乙基侧链的硅连接闭环复分解策略。对共同中间体32进行单独的脱硅基化和玉尾氧化，得到链唑啉和13-羟基链唑啉的前体。从氨基环戊烯醇（-）-7合成（+）-链唑啉1的总收率为4.8%，共16步。