通过杂-Pauson-Khand 环加成反应的（±）-Aplykurodinone-1 的全合成。

Formal Synthesis of (±)-Aplykurodinone-1 through a Hetero-Pauson-Khand Cycloaddition Approach.

机构信息

The State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou 730000, China.

Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University , Shenzhen 518055, China.

出版信息

Org Lett. 2017 Mar 3;19(5):1056-1059. doi: 10.1021/acs.orglett.7b00068. Epub 2017 Feb 20.

DOI:10.1021/acs.orglett.7b00068

PMID:28218858

Abstract

The tricyclic intermediate 2 has been synthesized in eight steps from known compound 6 in 20% overall yield. As such, this constitutes a highly efficient formal synthesis of (±)-aplykurodinone-1. This synthesis features a unique, one-pot, intramolecular hetero-Pauson-Khand reaction (h-PKR)/desilylation sequence to expeditiously construct the tricyclic framework, providing valuable insights for expanding the scope and boundaries of h-PKR.

摘要

三环中间体 2 已从已知化合物 6 经 8 步反应以 20%的总收率合成得到。因此，这构成了（±）-aplykurodinone-1 的高效正式合成。该合成具有独特的一锅法分子内杂 Pauson-Khand 反应（h-PKR）/脱硅序列，可以快速构建三环骨架，为扩展 h-PKR 的范围和边界提供了有价值的见解。