Phellilane L, Sesquiterpene Metabolite of Phellinus linteus: Isolation, Structure Elucidation, and Asymmetric Total Synthesis

J Org Chem. 2017 Dec 1;82(23):12377-12385. doi: 10.1021/acs.joc.7b02141. Epub 2017 Nov 9.

Abstract

A new cyclopropane-containing sesquiterpenoid, phellilane L (1), was isolated from the medicinal mushroom Phellinus linteus ("Meshimakobu" in Japanese), a member of the Hymenochaetaceae family and a well-known fungus that is widely used in East Asia. The planar structure of 1 was determined on the basis of spectroscopic analysis. The authors achieved the first total synthesis of 1. Our protecting group-free synthesis features a highly stereoselective one-pot synthesis involving an intermolecular alkylation/cyclization/lactonization strategy for construction of the key cyclopropane-γ-lactone intermediate. Additionally, our synthesis determined the absolute configuration of phellilane L (1).

MeSH terms

  • Agaricales / chemistry*
  • Basidiomycota / chemistry*
  • Chemistry, Pharmaceutical
  • Molecular Structure
  • Sesquiterpenes / chemistry*

Substances

  • Sesquiterpenes