Enantiospecific synthesis of B-seco-C-aromatic taxanes

Authors
Srikrishna, A Reddy, TJ Kumar, PP Gharpure, SJ
Citation
A. Srikrishna et al., Enantiospecific synthesis of B-seco-C-aromatic taxanes, I J CHEM B, 40(10), 2001, pp. 905-914
Citations number
28
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY
ISSN journal
03764699 → ACNP
Volume
40
Issue
10
Year of publication
2001
Pages
905 - 914
Database
ISI
SICI code
0376-4699(200110)40:10<905:ESOBT>2.0.ZU;2-5
Abstract
A simple and efficient methodology for the enantiospecific synthesis of B-s eco-C-aromatic taxanes starting from monoterpene (R)-carvone is described. Coupling of 6,6-dimethylcarvone 5 with appropriate arylethyl bromides follo wed by oxidation generates the enones 7, 15, 25, which are transformed into the 20-nor-B-seco-C-aromatic taxane derivatives 11, 17 and B-seco-C-aromat ic taxane derivative 29 via degradation of the isopropenyl group.