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Phosphorylated cyclopropanes in the synthesis of α-alkylidene-γ-butyrolactones: total synthesis of (±)-savinin, (±)-gadain and (±)-peperomin E
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Rh cyclopropane paper author accepted version
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| Journal | Organic and Biomolecular Chemistry |
|---|---|
| Date | Accepted/In press - 9 Aug 2016 |
| Date | E-pub ahead of print - 23 Aug 2016 |
| Date | Published (current) - 26 Sep 2016 |
| Issue number | 38 |
| Volume | 14 |
| Number of pages | 18 |
| Pages (from-to) | 8971-8988 |
| Early online date | 23/08/16 |
| Original language | English |
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.
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© 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.
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