4-Phenyl-4-methyl-2,2-dibutyl-1,3,2-dioxastannolane (4). The racemic compound was prepared from a commercial diol (Janssen, >98%; mp 44-45 °C), purified by crystallization; the 42% ee sample was prepared from an enriched diol, obtained following a known procedure:20 mp 93-95 °C. 13C NMR: Ph,

Evidence supporting the hypothesis that hydrolysis of the vinyl ether group of prostacyclin, accelerated by its carboxylic acid function operating in the carboxylate form, is responsible for the unusual hydrolytic lability of this substance is provided by the remarkably similar behaviour of (Z)-6,9-epoxynon-5-enoic acid; the latter is a simple model of prostacyclin which contains all of the structural features needed for this destabilization mechanism to function.

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