Stereoselective synthesis of a model C(18)-C(35) spiroketal fragment of integramycin

Org Lett. 2011 May 20;13(10):2734-7. doi: 10.1021/ol200834p. Epub 2011 Apr 21.

Abstract

A highly stereoselective synthesis of a model C(18)-C(35) spiroketal unit (7) of integramycin has been accomplished via an enantioselective stannyl-crotylboration reaction and an N-iodosuccinimide-mediated spiroketalization of 19a.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Furans / chemistry*
  • Models, Molecular*
  • Molecular Structure
  • Naphthalenes / chemistry*
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Stereoisomerism

Substances

  • Furans
  • Naphthalenes
  • Spiro Compounds
  • integramycin
  • spiroketal