Studies on the synthesis of apoptolidin A. 1. Synthesis of the C(1)-C(11) fragment

J Org Chem. 2008 Feb 1;73(3):1031-5. doi: 10.1021/jo702250z. Epub 2007 Dec 29.

Abstract

A synthesis of the C(1)-C(11) fragment of apoptolidin A has been accomplished by a convergent route involving the stereoselective glycosidation of 9 and the Suzuki cross-coupling reaction of bromodienoate 7 and the vinylborane generated via chemoselective hydroboration of diyne 6 with diisopinocampheylborane.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemical synthesis
  • Alkynes / chemistry
  • Carbon / chemistry*
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Molecular Structure
  • Propanols / chemical synthesis
  • Propanols / chemistry
  • Pyrones / chemical synthesis*
  • Pyrones / chemistry
  • Thioglycosides / chemical synthesis
  • Thioglycosides / chemistry

Substances

  • Alkynes
  • Macrolides
  • Propanols
  • Pyrones
  • Thioglycosides
  • apoptolidin A
  • Carbon
  • propargyl alcohol