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Synlett 1995; 1995(6): 607-608
DOI: 10.1055/s-1995-5018
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Synthesis of ent-Cheilanthenediol, the Enantiomer of a Natural Tricyclopentaprenediol

Thierry Jenn, Denis Heissler*
  • *Institut de Chimie, URA CNRS 31, Université Louis Pasteur, BP 296, 67008 Strasbourg, France
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Publication Date:
31 December 2000 (online)

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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.

Baylis-Hillman reaction - radical addition - cis double bond formation - epoxide opening - lithium diisobutyl-n-butyl-aluminium hydride