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α-Alkylidene-γ-butyrolactone synthesis via one-pot C-H insertion/olefination: Substrate scope and the total synthesis of (±)-cedarmycins A and B

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JournalTetrahedron
DateAccepted/In press - 28 Jul 2014
DatePublished (current) - 7 Oct 2014
Issue number39
Volume71
Number of pages16
Pages (from-to)7107-7123
Original languageEnglish

Abstract

A system for the synthesis of α-alkylidene-γ-butyrolactones via a one-pot C-H insertion/olefination sequence is described. The process is based on the rhodium catalysed C-H insertion reaction of α-diazo-α-(diethoxyphosphoryl)acetates. The mild reaction conditions, operational simplicity and ready availability of starting materials are all key features. A wide range of successful reaction systems are reported (41 examples) highlighting the generality of the method. The application of this method in the total synthesis of the natural products (±)-cedarmycins A and B is also described.

    Research areas

  • C-H insertion, Cedarmycins A and B, Rhodium carbenoids, Tandem reactions, α-Methylene-γ-butyrolactones

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