Oxidation with silver carbonate on Celite

Mechanism. Fetizon et al. have proposed a concerted mechanism for oxidations with silver carbonate on Celite in which the first step is a reversible absorption of the... 

In another synthesis the diol 155 was oxidized with silver carbonate on Celite to the lactone 156 convertible (lithium dimethyl cuprate, debenzylation, and dehydration) to ( )-eldanolide [( )-129]. Finally a synthesis of racemic eldanolide involved coupling of a C4 unit, 157, with 4-methyl-3-pentenal. In tetrahydrofuran at -78 C, the reaction occurred at the y-position to the metal atom (158) to yield 72% of the alcohol 159, which gave 98% ( )-129 with mercuric chloride. ... 

Inversion of the C-4 hydroxyl group on 805 and 807 would provide either of the lyxo-deoxyimino sugars 810 or 813. Deprotection of the OTBS groups on 802 followed by ozonolysis and oxidation with silver carbonate on Celite of the resulting anomeric mixture provides in 89% yield the lactone (li ,5i ,8R)-6-benzyl-8-hydroxy-2-oxa-6-azabicyclo-[3.3.0]octane-3,7-dione (808), determined by proton NMR of the MTPA ester to have 96% ee. 

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