Total synthesis of ent-dihydrocorynantheol by using a proline-catalyzed asymmetric addition reaction

Org Lett. 2006 Apr 13;8(8):1533-5. doi: 10.1021/ol0530575.

Abstract

[reaction: see text] 9-Tosyl-3,4-dihydro-beta-carboline reacted with 3-ethyl-3-buten-2-one in the presence of (S)-proline to give (3R,12bR)-3-ethyl-12-tosyl-3,4,6,7,8,9,10,11,12,12b-decahydro-1H-indolo[2,3-a]quinolizin-2-one in complete enantio- and diastereoselectivity. The compound thus obtained was readily transformed to ent-dihydrocorynantheol in three steps.

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Catalysis
  • Molecular Structure
  • Proline / chemistry*
  • Stereoisomerism

Substances

  • Alkaloids
  • dihydrocorynantheol
  • Proline