First total synthesis and stereochemical revision of laxaphycin B and its extension to lyngbyacyclamide A

Org Lett. 2013 Aug 2;15(15):3898-901. doi: 10.1021/ol401645m. Epub 2013 Jul 15.

Abstract

The first total synthesis of laxaphycin B was accomplished through stepwise automated Solid Phase Peptide Synthesis (SPPS), leading to the structural revision of its stereochemistry especially with regard to the configuration of one of the two 3-hydroxyleucines of this cyclic dodecapeptide of marine origin. The analogous Lyngbyacyclamide A was obtained by an extension of this synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry
  • Solid-Phase Synthesis Techniques
  • Stereoisomerism

Substances

  • Laxaphycin B
  • Peptides, Cyclic
  • lyngbyacyclamide A