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A concise total synthesis of xestodecalactone A, utilizing a Diels-Alder strategy is described. The focal Diels-Alder reaction relied on an "ynoate" dienophile to rapidly assemble the required resorcylinic acid scaffold. During this study, Diels-Alder cycloaddition reactions involving 1,3-disubstituted nonequivalent allene dienophiles were studied, and some surprising results were encountered.

Transesterification reactions of polyhydroxy compounds, such as 1-O-p-nitrobenzoyl-, 1-O-benzylglycerols, 1,2;3,4-di-O-, 3,4-O-isopropylidene-d-mannitols, 1,2-O-isopropylidene-α-d-glucofuranose, uridine, 1,2;5,6-di-O-isopropylidene-d-mannitol, and d-mannitol, by ethylene carbonate were attempted; the corresponding products were obtained in good yields except in the case of uridine, which gave 2,2′-anhydro-1-β-d-arabinofuranosyluracil.

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