Efficient synthesis of the C(1)-C(9) fragment of amphidinolides C, C2, and F.
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.
Ferrié
Laurent
L
UMR-8076 (BioCIS) Laboratoire de Pharmacognosie, Université Paris-Sud, Faculté de Pharmacie, Rue Jean-Baptiste Clément, 92296 Châtenay-Malabry, France. laurent.ferrie@u-psud.fr
Figadère
Bruno
B
D002244:Carbon / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism; D000097442:Amphidinolides
D002244:Carbon; D018942:Macrolides; C429132:amphidinolide C; D000097442:Amphidinolides; C555100:amphidinolide C2; C072156:amphidinolide F