Stereoselective cyclization assisted by the selenyl group. Biogenetic-type synthesis in the p-menthane series

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Abstract
Acid-catalysed cyclisation of the β-hydroxyselenide (3), derived from linalyl acetate (1), afforded the trans-p-menthanes (4) and (5), the structures of which were confirmed by their transformation into (6), (11), (8), and (13), and alternative syntheses of these compounds. The structure determination of some products obtained by the reaction of limonene and α-terpineol epoxides with phenylselenium anion was also carried out.

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