Total synthesis and structural confirmation of the marine natural product Dysinosin A: a novel inhibitor of thrombin and Factor VIIa

J Am Chem Soc. 2002 Nov 13;124(45):13342-3. doi: 10.1021/ja0208153.

Abstract

The structure and absolute configuration of the marine antithrombotic product dysinosin A was confirmed by total synthesis. The strategy involved disconnections to three subunits, of which two were synthesized from the readily available l-glutamic acid, d-leucine, and d-mannitol. The Grubbs olefin metathesis carbocyclization reaction was utilized to prepare two intermediates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Factor VIIa / antagonists & inhibitors*
  • Indoles / chemistry*
  • Indoles / isolation & purification
  • Indoles / pharmacology
  • Porifera / chemistry*
  • Pyrroles / chemistry*
  • Pyrroles / isolation & purification
  • Pyrroles / pharmacology
  • Serine Proteinase Inhibitors / chemical synthesis*
  • Thrombin / antagonists & inhibitors*

Substances

  • Indoles
  • Pyrroles
  • Serine Proteinase Inhibitors
  • dysinosin A
  • Factor VIIa
  • Thrombin