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Synlett 1992; 1992(2): 114-116
DOI: 10.1055/s-1992-21282
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Synthetic Studies Toward Paenoiflorin: Preparation of the Highly Functionalized Pinane Skeleton Utilizing Intramolecular Hosomi-Sakurai Reaction

Susumi Hatakeyama* , Mitsuhiro Kawamura, Eiji Shimanuki, Keiichi Saijo, Seiichi Takano
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980, Japan
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Publication Date:
08 March 2002 (online)

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An efficient route to the highly functionalized pinane unit present in paeniflorin (1) is described. The sequence employs the newly developed reagent, [4-(1,3-dithian-2-yl)-2-butenyl]trimethylsilane (6), which serves as an annulating agent by a combination of Michael addition and intramolecular Hosomi-Sakurai reaction.