cis-Decahydroquinolines via asymmetric organocatalysis: application to the total synthesis of lycoposerramine Z

Org Lett. 2013 Jan 18;15(2):326-9. doi: 10.1021/ol303257y. Epub 2012 Dec 27.

Abstract

A concise synthesis of the Lycopodium alkaloid lycoposerramine Z is reported. Key to the strategy is a one-pot organocatalyzed Michael reaction followed by a domino Robinson annulation/intramolecular aza-Michael reaction promoted by LiOH, leading to enantiopure cis-decahydroquinolines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Cyclic N-Oxides / chemical synthesis*
  • Cyclic N-Oxides / chemistry
  • Lycopodium / chemistry
  • Molecular Structure
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry
  • Stereoisomerism

Substances

  • Alkaloids
  • Cyclic N-Oxides
  • Quinolines
  • lycoposerramine-Z
  • decahydroquinoline-5-carboxylic acid