通过羟醛缩合反应实现帕马霉素 621A 的全合成。

An aldol approach to the total synthesis of pamamycin 621 A.

机构信息

State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

出版信息

Org Lett. 2009 Dec 17;11(24):5638-41. doi: 10.1021/ol902290v.

DOI:10.1021/ol902290v

PMID:19924871

Abstract

Pamamycin 621A was synthesized through a convergent route, with the THF rings constructed from Evans aldols in the presence of the chiral auxiliaries without suffering racemization or elimination. The basic amino group was introduced at a late stage through reduction of an azido group with n-Bu(3)SnH, which also demonstrates for the first time the great potential of this largely forgotten reduction protocol in synthesis of multifunctional substrates.

摘要

帕马霉素 621A 是通过会聚路线合成的，其中 THF 环是在手性助剂的存在下通过 Evans 羟醛缩合构建的，没有经历外消旋化或消除。碱性氨基是通过叠氮基团用 n-Bu(3)SnH 还原引入的，这也首次证明了这个在多功能底物合成中被广泛遗忘的还原方案的巨大潜力。