Lobocyclamide B from Lyngbya confervoides. Configuration and asymmetric synthesis of beta-hydroxy-alpha-amino acids by (-)-sparteine-mediated aldol addition

Org Lett. 2002 May 30;4(11):1883-6. doi: 10.1021/ol025876k.

Abstract

[reaction: see text] Lobocyclamide B, a cyclododecapeptide containing five beta-hydroxy-alpha-amino acid residues, was isolated from Lyngbya confervoides. This is the first reported occurrence of gamma-hydroxythreonine in a natural peptide. Optically active beta-hydroxy-alpha-amino acids required for configurational analysis of the title compound were prepared using a novel (-)-sparteine-mediated asymmetric aldol addition of N-(diphenylmethylene)glycine tert-butyl ester to aldehydes. The method is general for aliphatic and aryl aldehydes and notable for operational simplicity.

Publication types

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

MeSH terms

  • Amino Acids / chemistry*
  • Antifungal Agents / chemistry*
  • Antifungal Agents / isolation & purification
  • Chromatography, High Pressure Liquid
  • Cyanobacteria / chemistry*
  • Indicators and Reagents
  • Lithium / chemistry
  • Molecular Conformation
  • Optical Rotation
  • Sparteine / chemistry*

Substances

  • Amino Acids
  • Antifungal Agents
  • Indicators and Reagents
  • Sparteine
  • Lithium