Synthesis of balsaminone A, a naturally occurring pentacyclic dinaphthofuran quinone

J Org Chem. 2011 Oct 7;76(19):8082-7. doi: 10.1021/jo201395n. Epub 2011 Aug 29.

Abstract

A short synthesis of the natural product balsaminone A, a dinaphthofuran quinone, is described. The key steps of the synthesis are base-induced coupling of 1,4-dihydroxy-2-naphthaldehyde with 2,3-dichloronaphthoquinone to give a pentacyclic dinaphthofuran directly, followed by conversion of the aldehyde into the desired methoxy group via the corresponding phenol. The synthesis, in which the structure of a key pentacyclic intermediate is corroborated by X-ray crystallography, confirms the original structural assignment of the natural product.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry*
  • Chemistry Techniques, Synthetic / methods*
  • Naphthoquinones / chemical synthesis*
  • Naphthoquinones / chemistry*

Substances

  • Biological Products
  • Naphthoquinones
  • balsaminone A