Tetrahedron letters

Selective bond cleavage of [5.3. 1] propellanes by lead tetraacetate: A facile entry into the carbocyclic frame [A, B Ring] of taxol

P Kumar, AT Rao, K Saravanan, B Pandey

Index: Kumar, Pradeep; Rao, Ashok T.; Saravanan; Pandey, Bipin Tetrahedron Letters, 1995 , vol. 36, # 19 p. 3397 - 3400

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Citation Number: 12

Abstract

[5.3. 1] Propellanes eg, the tricyclo [5.3. 1.01, 7] undeca-2, 4-dien-10-one 8 and the corresponding methylidene compound 10 were prepared from methyl cinnamate 2 in several steps involving rhodium (II) acetate mediated cyclization of 4 to 6 as a key step. The selective central cyclopropyl bond cleavage in 8 and 10 by lead tetraacetate provides the basis of a new approach to the construction of carbocyclic frame of A, B ring of Taxol.