Efficient Preparation of Potentially Useful Chiral Cyclopentanoid Building Blocks Based on C2Symmetry
- 1 January 1990
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1990 (08) , 453-454
- https://doi.org/10.1055/s-1990-21123
Abstract
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.Keywords
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