Microwave-assisted Stille-coupling of steroidal substrates

Steroids. 2002 Jul;67(8):709-13. doi: 10.1016/s0039-128x(02)00026-0.

Abstract

Steroidal dienes were synthesised by Stille-coupling of the corresponding alkenyl iodides with vinyltributyltin under microwave irradiation in a domestic microwave oven in drastically reduced reaction times. Rate acceleration was observed also in the one-pot Stille-coupling-Diels-Alder reaction of 17-iodo-5alpha-androst-16-ene. Stereoselectivity of cycloaddition was slightly improved with diethyl maleate as the dienophile, compared to that achieved with thermal heating.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Alkenes / radiation effects
  • Hot Temperature
  • Iodides / chemistry*
  • Iodides / radiation effects
  • Maleates / chemistry
  • Microwaves*
  • Molecular Structure
  • Palladium / chemistry
  • Steroids / chemistry*
  • Steroids / radiation effects

Substances

  • Alkenes
  • Iodides
  • Maleates
  • Steroids
  • Palladium
  • diethyl maleate