A retro-Claisen approach to dolabriferol

Org Lett. 2006 Apr 27;8(9):1827-30. doi: 10.1021/ol060347s.

Abstract

[reaction: see text] The protected precursor 30 to dolabriferol was generated by a DBU-induced, ester-forming, retro-Claisen process. The required linear carbon chain present in 22 was synthesized by a stereoselective lithium aldol reaction. The necessary aldehyde and ketone fragments were synthesized using stereocontrolled aldol reactions with the ethyl (S)-lactate derived ketone 13.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Aplysia / chemistry
  • Molecular Structure
  • Pyrans / chemical synthesis*
  • Pyrans / chemistry
  • Pyrans / isolation & purification
  • Stereoisomerism

Substances

  • Pyrans
  • dolabriferol