Lloyd, Matthew G, Taylor, Richard J K orcid.org/0000-0002-5880-2490 and Unsworth, William P orcid.org/0000-0002-9169-5156 (2016) Phosphorylated cyclopropanes in the synthesis of α-alkylidene-γ-butyrolactones:total synthesis of (±)-savinin, (±)-gadain and (±)-peperomin E. Organic and Biomolecular Chemistry. pp. 8971-8988. ISSN 1477-0539
Abstract
Phosphorylated cyclopropanes, generated via the Rh(ii)-catalysed intramolecular cyclopropanation of α-(diethoxyphosphoryl)acetates, have been found to be useful precursors in the synthesis of α-alkylidene-γ-butyrolactones. These cyclopropyl intermediates undergo regioselective reductive ring-opening and subsequent Horner-Wadsworth-Emmons olefination to complete the synthesis. Total syntheses of (±)-savinin and (±)-gadain, as well as the first total synthesis of (±)-peperomin E, are all described using this method.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © Royal Society of Chemistry 2016. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details. |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 20 Oct 2016 09:20 |
Last Modified: | 31 Mar 2025 23:06 |
Published Version: | https://doi.org/10.1039/c6ob01527a |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1039/c6ob01527a |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:106259 |
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