Catalytic crossed Michael cycloisomerization of thioenoates: total synthesis of (+/-)-ricciocarpin A

Org Lett. 2003 May 15;5(10):1737-40. doi: 10.1021/ol030035e.

Abstract

[reaction: see text] Thioenoates are found to participate in highly chemoselective catalytic crossed Michael cycloisomerization with appendant aryl ketone and enoate partners to afford cyclopentene and cyclohexene products. This methodology has enabled a concise total synthesis of the potent molluscicide (+/-)-ricciocarpin A.

Publication types

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

MeSH terms

  • Catalysis
  • Cyclization
  • Furans / chemical synthesis*
  • Isomerism
  • Ketones / chemistry
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Molluscacides / chemical synthesis*
  • Plants / chemistry

Substances

  • Furans
  • Ketones
  • Molluscacides
  • ricciocarpin A