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Synlett 1994; 1994(8): 597-598
DOI: 10.1055/s-1994-22939
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Pd2+-Promoted Cyclization in Gibberellin Synthesis - A New Strategy for C20 Gibberellin Synthesis

Masahiro Toyota* , Toshihiro Wada, Youichi Nishikawa, Keiko Yanai, Keiichiro Fukumoto
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-77, Japan
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Publication Date:
18 September 2002 (online)

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The pentacyclic compound 7a, possessing the C20 gibberellin skeleton, is obtained via a 10-step synthetic sequence from 3-ethoxy-2-cyclohexen-1-one (2); the most interesting steps of the overall conversion involve Pd2+-promoted cyclization of the silyl enol ether of 3, and stereoselective intramolecular Diels-Alder reaction of the substrate 6.