Total synthesis of (+)-fastigiatine

J Am Chem Soc. 2010 Jul 21;132(28):9594-5. doi: 10.1021/ja104575h.

Abstract

The first total synthesis of the Lycopodium alkaloid (+)-fastigiatine has been accomplished in 15 steps and 30% overall yield from known compounds. Noteworthy transformations include a convergent fragment coupling via a nucleophilic cyclopropane opening, a highly diastereoselective formal [3 + 3]-cycloaddition, and a transannular Mannich reaction to construct the core of the natural product.

Publication types

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

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Lycopodium / chemistry*
  • Stereoisomerism

Substances

  • Alkaloids
  • fastigiatine