Organometallic Routes to Novel Steroids Containing Heterocyclic C-17 Side-Chains

Lucia Vitellozzi, Graeme D. McAllister, Thorsten Genski, Richard J K Taylor*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


A range of novel steroid analogues bearing a C-17 side-chain containing a 20R-hydroxyl group and a variety of heterocyclic substituents have been prepared by organometallic additions to 3-methoxypregnenolone. X-ray crystallography has been used to establish that the organometallic additions proceed with excellent Felkin-Anh control. This methodology has been extended, by use of the Achmatowicz rearrangement and ring-closing metathesis approaches, to prepare pyrandione and δ-lactone steroidal analogues reminiscent of the withanolide natural products.

Original languageEnglish
Pages (from-to)48-56
Number of pages9
Issue number1
Early online date2 Oct 2015
Publication statusPublished - 4 Jan 2016

Bibliographical note

© Georg Thieme Verlag. This is an author produced version of a paper published in Synthesis. Uploaded in accordance with the publisher's self-archiving policy.


  • Achmatowicz
  • heterocycles
  • metathesis
  • organometallic
  • steroid analogues
  • withanolides

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