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New strategy for the construction of a monotetrahydrofuran ring in Annonaceous acetogenin based on a ruthenium ring-closing metathesis: application to the synthesis of Solamin
Authors:Prestat Guillaume  Baylon Christophe  Heck Marie-Pierre  Grasa Gabriela A  Nolan Steven P  Mioskowski Charles
Institution:CEA, CE-Saclay, Service de Marquage Moléculaire et de Chimie Bioorganique, Bat 547, Département de Biologie Joliot-Curie, 91191 Gif Sur Yvette, France.
Abstract:An original convergent total synthesis of Solamin (type A annonaceous acetogenin) was achieved. The central THF core was obtained by means of a ring-closing metathesis (RCM) reaction using a ruthenium imidazolylidene complex. The RCM substrate was prepared from a vinyl-substituted epoxide by reaction with an allyl alcohol, both synthesized from propargylic alcohol. The flexibility of the strategy should be useful in preparing various natural and unnatural annonaceous acetogenins.
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