Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor

J Am Chem Soc. 2002 Oct 16;124(41):12078-9. doi: 10.1021/ja0276826.

Abstract

The asymmetric total synthesis of (-)-azaspirene, an angiogenesis inhibitor, has been accomplished, establishing its absolute stereochemistry. The key steps are a MgBr2.OEt2-mediated, diastereoselective Mukaiyama aldol reaction, a NaH-promoted, intramolecular cyclization of an alkynylamide, and the aldol reaction of a ketone containing functionalized gamma-lactam moiety without protection of tert-alcohol and amide functionalities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Angiogenesis Inhibitors / chemical synthesis*
  • Ascomycota / chemistry
  • Pyrrolidinones / chemical synthesis*
  • Spiro Compounds / chemical synthesis*
  • Stereoisomerism

Substances

  • Angiogenesis Inhibitors
  • Pyrrolidinones
  • Spiro Compounds
  • azaspirene