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Issue 38, 2016
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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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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.

Graphical abstract: Phosphorylated cyclopropanes in the synthesis of α-alkylidene-γ-butyrolactones: total synthesis of (±)-savinin, (±)-gadain and (±)-peperomin E

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Publication details

The article was received on 18 Jul 2016, accepted on 09 Aug 2016 and first published on 23 Aug 2016


Article type: Paper
DOI: 10.1039/C6OB01527A
Citation: Org. Biomol. Chem., 2016,14, 8971-8988
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    Phosphorylated cyclopropanes in the synthesis of α-alkylidene-γ-butyrolactones: total synthesis of (±)-savinin, (±)-gadain and (±)-peperomin E

    M. G. Lloyd, R. J. K. Taylor and W. P. Unsworth, Org. Biomol. Chem., 2016, 14, 8971
    DOI: 10.1039/C6OB01527A

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