Stereoselective synthesis of (-)-lepadins A-C

Chem Commun (Camb). 2013 Dec 7;49(94):11032-4. doi: 10.1039/c3cc46801a.

Abstract

A concise synthesis of the marine alkaloids (-)-lepadins A-C from a phenylglycinol-derived tricyclic lactam is reported. Key steps from the stereochemical standpoint involve stereoselective cyclocondensation, double bond hydrogenation, oxazolidine opening, hydroboration-oxidation, and Horner-Wadsworth-Emmons reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry*
  • Quinolines / chemical synthesis
  • Quinolines / chemistry
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Alkaloids
  • Quinolines
  • lepadin A
  • lepadin B
  • lepadin C