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

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

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.

Publication types

  • Research Support, Non-U.S. Gov't