Transition-metal-catalyzed synthesis of aspergillide B: an alkyne addition strategy

Org Lett. 2012 Mar 2;14(5):1322-5. doi: 10.1021/ol300200m. Epub 2012 Feb 22.

Abstract

A catalytic enantioselective formal total synthesis of aspergillide B is reported. This linchpin synthesis was enabled by the development of new conditions for Zn-ProPhenol catalyzed asymmetric alkyne addition. This reaction was used in conjunction with ruthenium-catalyzed trans-hydrosilylation to affect the rapid construction of a late-stage synthetic intermediate of aspergillide B to complete a formal synthesis of aspergillide B in a highly efficient manner.

Publication types

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

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Macrolides / chemical synthesis*
  • Molecular Structure
  • Stereoisomerism
  • Transition Elements / chemistry*

Substances

  • Alkynes
  • Macrolides
  • Transition Elements
  • aspergillide B