Vitellozzi, Lucia, McAllister, Graeme D., Genski, Thorsten et al. (1 more author) (2016) Organometallic Routes to Novel Steroids Containing Heterocyclic C-17 Side-Chains. SYNTHESIS-STUTTGART. pp. 48-56. ISSN 0039-7881
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.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 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. |
Keywords: | Achmatowicz,heterocycles,metathesis,organometallic,steroid analogues,withanolides |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) The University of York |
Depositing User: | Pure (York) |
Date Deposited: | 19 Jan 2016 00:01 |
Last Modified: | 15 Mar 2025 00:06 |
Published Version: | https://doi.org/10.1055/s-0035-1560353 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1055/s-0035-1560353 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:93901 |