Synthesis of the Prelog-Djerassi lactone via an asymmetric hydroformylation/crotylation tandem sequence

Org Lett. 2012 May 18;14(10):2572-5. doi: 10.1021/ol3008765. Epub 2012 May 4.

Abstract

A synthesis of the Prelog-Djerassi lactone [(+)-1] has been accomplished in three isolations and 57% overall yield from the known vinyl ortho ester 2. A Rh(I)-catalyzed asymmetric hydroformylation/crotylation tandem sequence has been developed and used to set the C2-C4 stereochemistry. A Rh(I)-catalyzed asymmetric hydrogenation was employed to set the C6 sterechemistry, resulting in an unusually short and efficient enantioselective synthesis of this touchstone molecule from achiral starting material.

Publication types

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

MeSH terms

  • Catalysis
  • Esters
  • Hydrogenation
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Molecular Structure
  • Rhodium / chemistry
  • Stereoisomerism

Substances

  • Esters
  • Lactones
  • Rhodium