A new total synthesis of the marine tunicate alkaloid lepadiformine

Org Lett. 2001 Nov 1;3(22):3507-10. doi: 10.1021/ol010179y.

Abstract

[reaction: see text]. A total synthesis of racemic lepadiformine has been achieved via a route that utilizes as key steps a novel stereocontrolled intramolecular spirocyclization of an allylsilane/N-acyliminium ion and the application of our radical-based methodology for production of N-acylimines from o-aminobenzamides.

Publication types

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

MeSH terms

  • Alkaloids / chemical synthesis*
  • Animals
  • Cardiovascular Agents / chemical synthesis*
  • Crystallography, X-Ray
  • Cyclization
  • Indicators and Reagents
  • Urochordata / chemistry*

Substances

  • Alkaloids
  • Cardiovascular Agents
  • Indicators and Reagents
  • lepadiformine