Preparation of cis-γ-hydroxycarvone Derivatives for Synthesis of Sesterterpenoid Natural Products: Total Synthesis of Phorbin A

J Org Chem. 2015 Feb 20;80(4):2231-9. doi: 10.1021/jo502748s. Epub 2015 Feb 5.

Abstract

A robust synthetic approach to cis-γ-hydroxycarvone derivatives has been developed, enabling efficient access to synthetic building blocks for the growing family of bioactive sesterterpenoid natural products. Using this approach, an allyl bromide carvone derivative was used as the key building block for the total synthesis of the natural product phorbin A. This synthetic sequence also demonstrates the utility of benozyl enol ethers as an effective means of masking a β-ketophosphonate and their subsequent application in a one-pot benzoyl transfer-intramolecular Horner-Wadsworth-Emmons reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Molecular Structure
  • Monoterpenes / chemical synthesis*
  • Monoterpenes / chemistry
  • Sesterterpenes / chemical synthesis*
  • Sesterterpenes / chemistry
  • Stereoisomerism

Substances

  • Biological Products
  • Monoterpenes
  • Sesterterpenes
  • phorbin A