Journal of the Chemical Society. Perkin transactions I p. 2055 - 2058 (1981)
Update date:2022-08-02
Topics:
Newton, Roger F.
Reynolds, Derek P.
Webb, Colin F.
Roberts, Stanley M.
Baeyer-Villiger oxidation of the bicyclo<2.2.1>heptanone (4; R = SiMe2But) afforded a mixture of isomeric lactones (5) and (6), the minor component (6) being conveniently removed by selective hydrolysis.Reduction of the lactone (5) by di-isobutylaluminium hydride gave the corresponding lactol (8).Conversion of (8) into the 9α-silyloxyprostanoid (10) was performed so as to minimise silyl group migration.Oxidation to (10) gave the ketone (12) but the hindered siloxy-group at C-9 was extremely resistant to cleavage by the usual reagents.Satisfactory deprotection of (12) was achieved by treatment with aqueous HF in acetonitrile to give (+/-)-prostaglandin D2 methyl ester (14) and (+/-)-15-epi-prostaglandin D2 methyl ester (15).The high 'silicophilicity' and low acidity of HF make it the reagent of choice for cleavage of silyl ethers under mildly acidic conditions.
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