A concise, selective synthesis of the polyketide spacer domain of a potent bryostatin analogue

Org Lett. 2003 Feb 6;5(3):277-9. doi: 10.1021/ol0272390.

Abstract

[reaction: see text] A concise, asymmetric synthesis of the polyketide spacer domain portion (C1-C13) of a highly potent bryostatin analogue was developed. The route utilizes asymmetric hydrogenation methodology to install the C3, C5, and C11 stereocenters, while a substrate directed syn reduction sets the C9 stereocenter. The spacer domain 1 is obtained in 10 steps with a 25% overall yield and is readily incorporated into the synthesis of 2.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Bryostatins
  • Lactones / chemical synthesis*
  • Lactones / chemistry*
  • Macrolides
  • Molecular Structure

Substances

  • Bryostatins
  • Lactones
  • Macrolides
  • bryostatin 1