Efficient synthesis of the C(1)-C(9) fragment of amphidinolides C, C2, and F |
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Authors: | Ferrié Laurent Figadère Bruno |
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Affiliation: | UMR-8076 (BioCIS) Laboratoire de Pharmacognosie, Universite? Paris-Sud, Faculte? de Pharmacie, Rue Jean-Baptiste Cle?ment, 92296 Cha?tenay-Malabry, France. laurent.ferrie@u-psud.fr |
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Abstract: | The synthesis of the C(1)-C(9) fragment of amphidinolides C, C2, and F was achieved by using a vinyloguous Mukaiyama aldol reaction on a chiral aldehyde with a silyloxyfuran and by using a C-glycosylation of a lactol derivative with an acetyl oxazolidinethione. From the available chiral acetonide-glyceraldehyde, all the stereogenic centers were perfectly induced along the synthesis. The C(1)-C(9) fragment was synthesized as a vinyl stannane at C(9) in 10 steps, with 16% yield. |
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