IMPROVED ACCESS TO 19-NOR-7-BETA,8-BETA-METHYLENE-TAXOIDS AND FORMATION OF A 7-MEMBERED C-RING ANALOG OF DOCETAXEL BY ELECTROCHEMISTRY

Authors
BOUCHARD H PULICANI JP VUILHORGNE M BOURZAT JD COMMERCON A
Citation
H. Bouchard et al., IMPROVED ACCESS TO 19-NOR-7-BETA,8-BETA-METHYLENE-TAXOIDS AND FORMATION OF A 7-MEMBERED C-RING ANALOG OF DOCETAXEL BY ELECTROCHEMISTRY, Tetrahedron letters, 35(52), 1994, pp. 9713-9716
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
52
Year of publication
1994
Pages
9713 - 9716
Database
ISI
SICI code
0040-4039(1994)35:52<9713:IAT1AF>2.0.ZU;2-2
Abstract
A new route to semisynthetic 19-nor-7 beta, 8 beta-methylene taxoids, such as compound 8, from the 7-O-trifluoromethanesulfonyl derivative 6 is reported. Evidence for a dissociation of the triflate to form a ca rbocation at C-7 under the reaction conditions is presented. Electroch emical reduction of the cyclopropane taxoid 8 gives, besides the expec ted 10-dehydroxy-cyclopropane analog 10, the 7-membered C-ring derivat ive 11.