Rapid assembly of the polyhydroxylated beta-amino acid constituents of microsclerodermins C, D, and E

Org Lett. 2008 Mar 6;10(5):841-4. doi: 10.1021/ol702962z. Epub 2008 Feb 7.

Abstract

A very short and efficient synthesis of protected derivatives of APTO and AETD, the complex polyhydroxylated beta-amino acid residues present in microsclerodermins C, D, and E, is described. The targets are obtained in only five steps, in 23% and 16% overall yields, respectively. The key transformation involves the completely diastereoselective two-carbon homologation of appropriately selected intermediate chiral sulfinimines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Animals
  • Imines / chemistry
  • Molecular Structure
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry
  • Porifera / chemistry
  • Stereoisomerism
  • Sulfonium Compounds / chemistry

Substances

  • Amino Acids
  • Imines
  • Peptides, Cyclic
  • Sulfonium Compounds
  • microsclerodermin C
  • microsclerodermin D
  • microsclerodermin E
  • sulfinimine