Stereoselective construction of a beta-isopropenyl alcohol moiety at the C(2) and (3) of kallolide A and pinnatin a using a [2,3] Wittig rearrangement of cyclic furfuryl ethers

J Org Chem. 2003 Dec 26;68(26):10183-6. doi: 10.1021/jo035244r.

Abstract

A stereocontrolled synthesis of anti- and syn-beta-isopropenyl alcohol moieties at the C(2)-C(3) positions of kallolide A and pinnatin A was accomplished employing the [2,3] Wittig rearrangement of (E)-and (Z)-cyclic furfuryl ethers 8. Enantioselective Wittig rearrangement of (E)- and (Z)-furfuryl ethers 8 using butyllithium and a chiral bis(oxazoline) was also examined to provide (2R,3R)-homoallylic alcohol anti-9 in up to 61% ee and (2R,3S)-syn-9 in up to 93% ee, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Diterpenes / chemistry*
  • Ethers, Cyclic / chemistry*
  • Furans / chemistry*
  • Molecular Structure
  • Propanols / chemical synthesis*
  • Propanols / chemistry
  • Stereoisomerism

Substances

  • Diterpenes
  • Ethers, Cyclic
  • Furans
  • Propanols