Enantioselective total synthesis of (+)-leucascandrolide A macrolactone

Org Lett. 2003 Nov 27;5(24):4641-4. doi: 10.1021/ol035797o.

Abstract

[reaction: see text] The enantioselective synthesis of the (+)-leucascandrolide A macrolactone has been achieved in 20 linear steps from 1,3-propanediol. The key steps in the synthesis are a reductive cleavage of bicyclic ketal 5 to establish the C15 stereogenic center and a diastereoselective aldol of the boron enolate of methyl ketone 3 to aldehyde 4 in preparation for a heteroconjugate addition for the introduction of the C3 stereocenter.

Publication types

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

MeSH terms

  • Aldehydes / chemical synthesis
  • Aldehydes / chemistry
  • Ketones / chemistry
  • Molecular Structure
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Ketones
  • Sesquiterpenes
  • leucascandrolide A