Synthesis of ent-Cheilanthenediol, the Enantiomer of a Natural Tricyclopentaprenediol

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Abstract
This synthesis of the sesterterpene ent-cheilanthenediol is based on the addition of the isocopal-12-en-15-yl radical to monoprotected methyl 3,4-dihydroxy-2-methylenebutanoate which has been prepared from protected hydroxyacetaldehyde by a Baylis-Hillman reaction. The equatorial tertiary hydroxyl group at C-13 has been obtained by opening an epoxide with lithium diisobutyl-n-butylaluminium hydride.

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