Synthesis of substituted indans as prostacyclin analogues

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Abstract
A route is described to the substituted indans (8) and (10), prepared as analogues of prostaglandin I2(prostacyclin). Two key steps in the synthesis involve the regiospecific attack of lithium salts from allylic sulphides onto indene oxides and, after oxidation to the corresponding sulphoxides, their reductive rearrangement to the required diols. Using model indene oxides, attempts have been made to direct the stereochemistry of the exocyclic hydroxy group by steric control during formation of the precursor sulphide.