Lobocyclamide B from Lyngbya confervoides. Configuration and Asymmetric Synthesis of β-Hydroxy-α-amino Acids by (-)-Sparteine-Mediated Aldol Addition

John B. MacMillan, Tadeusz F. Molinski

Research output: Contribution to journalArticle

57 Scopus citations

Abstract

(Matrix Presented) Lobocyclamide B, a cyclododecapeptide containing five β-hydroxy-α-amino acid residues, was isolated from Lyngbya confervoides. This is the first reported occurrence of γ-hydroxythreonine in a natural peptide. Optically active β-hydroxy-α-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.

Original languageEnglish (US)
Pages (from-to)1883-1886
Number of pages4
JournalOrganic Letters
Volume4
Issue number11
DOIs
StatePublished - May 30 2002

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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