Regiocontrol in an intramolecular Schmidt reaction: total synthesis of (+)-aspidospermidine

Org Lett. 2000 Jun 1;2(11):1625-7. doi: 10.1021/ol005913c.

Abstract

[reaction--see text] A total synthesis of (+)-aspidospermidine (1) is described, featuring an intramolecular Schmidt reaction as the key step. The effects of stereochemistry and protecting group status on the regio- and chemoselectivity of this reaction were examined.

Publication types

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

MeSH terms

  • Alkaloids / chemical synthesis
  • Alkaloids / chemistry
  • Indole Alkaloids
  • Indoles*
  • Quinolines*
  • Spermidine / analogs & derivatives*
  • Spermidine / chemical synthesis
  • Spermidine / chemistry*
  • Stereoisomerism

Substances

  • Alkaloids
  • Indole Alkaloids
  • Indoles
  • Quinolines
  • aspidospermidine
  • Spermidine