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Synthesis of (+) dictyopterene a constituent of marine brown algae and (+) dictyopterene C′ by chirality transfer of optically active allylic benzoate with palladium (O) catalyst.
Authors:Françoise Colobert  Jean-Pierre Genet
Affiliation:Laboratoire de Synthése Orqanique et Organométallique Associé C.N.R.S Université, Pierre et Marie Curie - 75005 - Paris France
Abstract:The first enantioselective syntheses of (+) dictyopterene A 1 and (+)dictyopterene C′ were reported. The key reaction was based on palladium promoted cyclisation of chiral allylic benzoate 5 with transfer of chirality (anti attack of the palladium with respect to the leaving group) to give optically active vinylcyclopropane 7 with (R) configuration which contains proper functionality for further elaboration into 1 and 3
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