Selective bond cleavage of [5.3.1]propellanes by lead tetraacetate: A facile entry into the carbocyclic frame [A,B ring] of taxol

Article abstract of DOI:10.1016/0040-4039(95)00491-T

[5.3.1]Propellanes e.g., the tricyclo[5.3.1.0^1,7]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 carbocylic frame of A,B ring of Taxol.