Emeriones A-C: Three Highly Methylated Polyketides with Bicyclo[4.2.0]octene and 3,6-Dioxabicyclo[3.1.0]hexane Functionalities from Emericella nidulans

Org Lett. 2019 Jul 5;21(13):5091-5095. doi: 10.1021/acs.orglett.9b01680. Epub 2019 Jun 19.

Abstract

Emeriones A-C (1-3), three highly methylated polyketides with bicyclo[4.2.0]octene and 3,6-dioxabicyclo[3.1.0]hexane functionalities, were isolated from Emericella nidulans. An additional peroxide bridge in compound 3 led to the construction of an unexpected 7,8-dioxatricyclo[4.2.2.02,5]decene scaffold. The structures of 1-3 were elucidated by comprehensive spectroscopic techniques, and their absolute configurations were confirmed by single-crystal X-ray crystallographic analyses and ECD calculations. Compound 1 shows weak inhibitory effects on NO production in LPS-induced RAW264.7 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Emericella / chemistry*
  • Hexanes / chemistry*
  • Methylation
  • Models, Molecular
  • Molecular Conformation
  • Polyketides / chemistry*

Substances

  • Alkenes
  • Hexanes
  • Polyketides