SELECTIVE BOND-CLEAVAGE OF [5.3.1]PROPELLANES BY LEAD-TETRAACETATE - A FACILE ENTRY INTO THE CARBOCYCLIC FRAME [A,B RING] OF TAXOL

Authors
KUMAR P RAO AT SARAVANAN K PANDEY B
Citation
P. Kumar et al., SELECTIVE BOND-CLEAVAGE OF [5.3.1]PROPELLANES BY LEAD-TETRAACETATE - A FACILE ENTRY INTO THE CARBOCYCLIC FRAME [A,B RING] OF TAXOL, Tetrahedron letters, 36(19), 1995, pp. 3397-3400
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
19
Year of publication
1995
Pages
3397 - 3400
Database
ISI
SICI code
0040-4039(1995)36:19<3397:SBO[BL>2.0.ZU;2-P
Abstract
[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 fro m methyl cinnamate 2 in several steps involving rhodium(II) acetate me diated cyclization of 4 to 6 as a key step. The selective central cycl opropyl bond cleavage in 8 and 10 by lead tetraacetate provides the ba sis of a new approach to the constriction of carbocyclic frame of A,B ring of Taxol.