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Synlett 1990; 1990(8): 453-454
DOI: 10.1055/s-1990-21123
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Efficient Preparation of Potentially Useful Chiral Cyclopentanoid Building Blocks Based on C2 Symmetry

Seiichi Takano* , Takumichi Sugihara, Kunio Ogasawara
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980, Japan
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Publication Date:
08 March 2002 (online)

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Based on C 2 symmetry of the chiral substrate (2R,7R)-1,8-dibenzyloxy-3,5-octadiyn-2,7-diol (8) obtained from the dimerization of the chiral (3R)-4-benzyloxy-1-butyn-3-ol (4), the potentially useful trisubstituted cyclopentanoids, (3R,4R)-3,4- bis 3-benzyloxy-l-propenyl)cyclopentanone (12) and -cyclopentanol (13), have been prepared efficiently in satisfactory yields. Key steps are a diastereoselective [3,3]-sigmatropic rearrangement and a Dieckmann condensation.

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