Total Synthesis of Anmindenol A and Its Application to the Design, Synthesis, and Biological Evaluation of Derivatives Thereof

J Org Chem. 2019 Sep 6;84(17):10953-10961. doi: 10.1021/acs.joc.9b01564. Epub 2019 Aug 12.

Abstract

The first total synthesis of anmindenol A is described in four steps. A notable feature of the synthetic route includes the efficient construction of the 3,10-dialkylsubstituted benzofulvene core via a stereoselective vinylogous Stork enamine aldol condensation. The strategy provided a blueprint for the practical preparation of derivatives with modifications in the C-10 alkyl substituents. The novel derivatives inhibited nitric oxide production in stimulated RAW 264.7 macrophage cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemistry Techniques, Synthetic
  • Drug Design*
  • Indenes / chemical synthesis*
  • Indenes / chemistry*
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry*

Substances

  • Indenes
  • Sesquiterpenes
  • anmindenol A