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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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JournalOrganic and Biomolecular Chemistry
DateAccepted/In press - 9 Aug 2016
DateE-pub ahead of print - 23 Aug 2016
DatePublished (current) - 26 Sep 2016
Issue number38
Volume14
Number of pages18
Pages (from-to)8971-8988
Early online date23/08/16
Original languageEnglish

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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