A Cyclopentane, Cyclopentene and Cyclopentanone Annulation Methodology

References

• For a recent account of a variety of synthetic approaches, see: Symposia-in-Print, Number 3, edited by L. A. Paquette, Tet., (1981), 37, No. 25
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• Prof. Paquette also provides a lively discussion of cyclopentanoid chemistry in Topics in Current Chemistry, L. A. Paquette, (1979), 79, 41–165
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• Singh , P. and Weinreb , S. M. 1976 . Tet. , 32 : 2379
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• Cooke , M. P. Jr. 1981 . Tetrahedron Letters , : 381
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• Svendsen , A. and Boll , P. M. 1973 . Tet. , 28 : 4251
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• Chamot , E. and Paquette , L. A. 1978 . J. Org. Chem. , 43 : 4527 Paquette has used the corresponding anhydride, (i), in a Diels-Alder reaction
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• Dauben , W. G. , Kessel , C. R. and Takamura , K. H. 1980 . J. Am. Chem. Soc. , 102 : 6893 The high-pressure cycloaddition of ii with furan has provided a simple synthesis of cantharidin
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• A likely mechanism for this conversion is shown below:
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• An unambiguous synthesis of 8 confirmed its structure:
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