11-Step Total Synthesis of Pallambins C and D

J Am Chem Soc. 2016 Jun 22;138(24):7536-9. doi: 10.1021/jacs.6b04816. Epub 2016 Jun 10.

Abstract

The structurally intriguing terpenes pallambins C and D have been assembled in only 11 steps from a cheap commodity chemical: furfuryl alcohol. This synthesis, which features a redox-economic approach free of protecting-group manipulations, assembles all four-ring systems via a sequential cyclization strategy. Of these four-ring constructing operations, two are classical (Robinson annulation and Mukaiyama aldol) and two are newly devised. During the course of this work a method for the difunctionalization of enol ethers was developed, and the scope of this transformation was explored.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Chemistry Techniques, Synthetic / methods*
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Furans / chemistry*
  • Molecular Structure
  • Oxidation-Reduction

Substances

  • Diterpenes
  • Furans
  • pallambin C
  • pallambin D
  • furfuryl alcohol