A new enantiospecific synthetic procedure to the taxoid-intermediate 10-methylenecamphor, and 10-methylenefenchone

A new straightforward enantiospecific synthetic procedure to both 10-methylenecamphor and 10-methylenefenchone, from (+)-camphor and (−)-fenchone, respectively, is described. 10-Methylenecamphor is the key intermediate in Paquette's approach to taxol and taxusin, whereas 10-methylenefenchone co...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2002-02, Vol.13 (1), p.17-19
Main Authors: Garcı́a Martı́nez, Antonio, Teso Vilar, Enrique, Garcı́a Fraile, Amelia, de la Moya Cerero, Santiago, Lora Maroto, Beatriz
Format: Article
Language:English
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Summary:A new straightforward enantiospecific synthetic procedure to both 10-methylenecamphor and 10-methylenefenchone, from (+)-camphor and (−)-fenchone, respectively, is described. 10-Methylenecamphor is the key intermediate in Paquette's approach to taxol and taxusin, whereas 10-methylenefenchone could be a convenient intermediate to a new family of potentially interesting taxoids. The key steps of the described procedure are: (a) stereocontrolled tandem electrophilic carboncarbon double-bond addition-Wagner–Meerwein rearrangement of a camphor- or fenchone-derived 2-methylenenorbornan-1-ol under Eschenmoser's salt treatment, and (b) Cope elimination for generation of the vinyl group at the bridgehead norbornane position. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(02)00049-6