通过酰胺丙烯醛环加成反应全合成免疫抑制剂FR901483。

Total synthesis of the immunosuppressant FR901483 via an amidoacrolein cycloaddition.

作者信息

Maeng J H, Funk R L

机构信息

Department of Chemistry, Pennsylvania State University, University Park, Pennsylvania 16801, USA.

出版信息

Org Lett. 2001 Apr 19;3(8):1125-8. doi: 10.1021/ol015506g.

DOI:10.1021/ol015506g

PMID:11348175

Abstract

[reaction: see text]. The total synthesis of the potent immunosuppressant FR901483 is described. In a key step, the intermolecular Diels-Alder cycloaddition of an amidoacrolein with 2-(triisopropylsilyloxy)-1,3-butadiene produced the desired 3-cyclohexene-1-carboxaldehyde. This compound was subjected to basic followed by acidic conditions which effected two sequential aldol cyclizations to deliver the tricyclic ring system of the natural product, suitably functionalized for completion of the total synthesis.

摘要

[反应：见正文]。描述了强效免疫抑制剂FR901483的全合成。在关键步骤中，酰胺丙烯醛与2-(三异丙基甲硅烷氧基)-1,3-丁二烯的分子间狄尔斯-阿尔德环加成反应生成了所需的3-环己烯-1-甲醛。该化合物先在碱性条件下处理，然后在酸性条件下处理，这导致了两个连续的羟醛环化反应，从而得到了天然产物的三环环系，并进行了适当的官能团化以完成全合成。