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Synlett 1990; 1990(11): 667-669
DOI: 10.1055/s-1990-21203
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Stereoselective Access to the Basic Skeleton of Tetracyclic Diterpenes via a Sequence of Consecutive [3+2], [2+2+2], and [4+2] Cycloaddition Reactions. Studies on the Stereoselectivity of the Intramolecular Diels-Alder Reaction

Jean-Pierre Gotteland* , Max Malacria
  • *Université Pierre et Marie Curie - Paris VI, Laboratoire de Chimie Organique de Synthèse, associé au CNRS, Tour 44-54, 4 Place Jussieu, F-75252 Paris Cedex 05, France
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Publication Date:
08 March 2002 (online)

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1-{ 2-[2,2-Bis(methoxycarbonyl)-4-methylenecyclopentyl]-2-oxoethyl}-4,5-bis(trimethylsilyl)benzocyclobutene (16) and its acetal 17, prepared in a sequence involving Trost's [3+2] annelation and Vollhardt's [2+2+2] cycloaddition, underwent an intramolecular Diels-Alder reaction to afford the basic skeleton of tetracyclic diterpenes kaurane and phyllocladane. The carbonyl group at C-12 favored the kaurane stereochemistry (58:42), whereas the acetal function at that position led to a highly stereoselective formation of the phyllocladane stereochemistry (97:3).