First total synthesis of leucamide A

J Org Chem. 2003 Feb 21;68(4):1636-9. doi: 10.1021/jo026799+.

Abstract

The first total synthesis of marine bioactive cyclic heptapeptide Leucamide A has been accomplished, including a simple method for construction of the 4,2-bisheterocycle tandem pair substructure that employs a DAST-mediated cyclization of beta-hydroxy amide and final HBTU-promoted ring closing.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Catalysis
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Peptides, Cyclic / chemical synthesis*
  • Porifera / chemistry
  • Stereoisomerism

Substances

  • Peptides, Cyclic
  • leucamide A