Cascade polyketide and polyene cyclizations: biomimetic total synthesis of hongoquercin B

J Am Chem Soc. 2014 Dec 10;136(49):17013-5. doi: 10.1021/ja511534x. Epub 2014 Dec 1.

Abstract

The total synthesis of hongoquercin B was carried out in 9 steps from trans,trans-farnesyl acetate using a palladium catalyzed decarboxylative π-farnesyl rearrangement of a diketo-dioxinone ester, aromatization and cationic diene-epoxide cyclization as key steps. This cascade tetracyclization simplifies the synthesis of terpenoid resorcylate natural products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Molecular Conformation
  • Polyenes / chemistry*
  • Polyketides / chemistry*
  • Sesquiterpenes / chemical synthesis
  • Sesquiterpenes / chemistry
  • Stereoisomerism

Substances

  • Polyenes
  • Polyketides
  • Sesquiterpenes
  • hongoquercin B