An efficient total synthesis of (+/-)-lycoramine

Org Lett. 2004 Dec 9;6(25):4691-4. doi: 10.1021/ol048105k.

Abstract

[reaction: see text] A short and unique approach to (+/-)-lycoramine as one of the galanthamine-type alkaloids has been efficiently developed. The alternative advantage lies in that three stereocenters, including a crucial quaternary carbon center, were constructed with high diasteroselectivity via a key one-step NBS-mediated semipinacol rearrangement of the allylic alcohol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amaryllidaceae Alkaloids / chemical synthesis*
  • Amaryllidaceae Alkaloids / chemistry
  • Cyclization
  • Molecular Structure
  • Propanols / chemistry
  • Stereoisomerism

Substances

  • Amaryllidaceae Alkaloids
  • Propanols
  • allyl alcohol
  • lycoramine