The total synthesis of (+/-)-citreoviral, which co-occurs with citreoviridin, citreoviridinol, and citreodiol in Penicillium citreoviride, is described. The synthesis is based on a biogenetic model, and has as a key feature the elaboration of the dihydroxytetrahydrofuranyl ring portion 10 by an acid-catalysed cyclisation of the central epoxy alcohol intermediate 9 which is derived in ten steps from methyl tiglate.
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Ecole Super Phys & Chim Ind Ville Paris, Chim Organ Lab, CNRS, F-75231 Paris 05, FranceEcole Super Phys & Chim Ind Ville Paris, Chim Organ Lab, CNRS, F-75231 Paris 05, France
Cossy, J
Bauer, D
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Ecole Super Phys & Chim Ind Ville Paris, Chim Organ Lab, CNRS, F-75231 Paris 05, FranceEcole Super Phys & Chim Ind Ville Paris, Chim Organ Lab, CNRS, F-75231 Paris 05, France
Bauer, D
Bellosta, V
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Ecole Super Phys & Chim Ind Ville Paris, Chim Organ Lab, CNRS, F-75231 Paris 05, FranceEcole Super Phys & Chim Ind Ville Paris, Chim Organ Lab, CNRS, F-75231 Paris 05, France