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

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JournalSYNTHESIS-STUTTGART
DateE-pub ahead of print - 2 Oct 2015
DatePublished (current) - 4 Jan 2016
Issue number1
Volume48
Number of pages9
Pages (from-to)48-56
Early online date2/10/15
Original languageEnglish

Abstract

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.

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© 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.

    Research areas

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

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