The 5-8-5-membered tricyclic diterpene, cycloaraneosene, has been totally synthesized via the stereoselective condensation of two units of optically active iridoids, Cope rearrangement and chemical reduction of the tetrasubstituted C=C bond. The NMR spectrum of synthetic 9α-hydroxycycloaraneosene was not identical with the congener product, and the natural alcohol is likely to be 8β-hydroxyl derivative.
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Kato et al. (1986) studied this question.
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