Substituted 1,7-dioxabicyclo[3.3.0]octanes: New easy access to the perhydrofurofuran core of aflatoxins and analogues

Article abstract of DOI:10.1016/S0040-4039(97)00278-5

The reaction of 3-chloro-2-(chloromethyl)-1-propene (1) with lithium and a catalytic amount of naphthalene in the presence of different carbonyl compounds in THF a -78°C affords, after hydrolysis, the corresponding methylenic diols 2, which by a tandem hydroboration-oxidation with hydrogen peroxide followed by treatment with PCC (for ketone derivatives) or RuCl₂(PPh₃)₃ (for aldehyde derivatives) yields the expected perhydrofurofurans 3.