Total synthesis of the immunosupressant (-)-pironetin (PA48153C)

Org Lett. 2001 Mar 8;3(5):707-10. doi: 10.1021/ol015531m.

Abstract

[reaction: see text]. Total synthesis of the immunosuppresant pironetin has been achieved by a synthetic route in which the connections between starting materials and the desired structure are readily discerned. Key steps include a diastereoselective Lewis acid mediated crotylstannane aldehyde addition, a highly selective Lewis acid promoted Mukaiyama aldol reaction, an anti-selective SmI2 reduction of a beta-hydroxyketone, and finally a lactone annulation reaction.

Publication types

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

MeSH terms

  • Immunosuppressive Agents / chemical synthesis*
  • Indicators and Reagents
  • Pyrones / chemical synthesis*
  • Streptomyces / chemistry

Substances

  • Immunosuppressive Agents
  • Indicators and Reagents
  • Pyrones
  • pironetin