THE DEVELOPMENT OF STRATEGIES FOR CONSTRUCTION OF THE AZIRIDINE CORE OF THE ANTITUMOR AGENTS AZINOMYCIN-A AND AZINOMYCIN-B

Authors
COLEMAN RS CARPENTER AJ
Citation
Rs. Coleman et Aj. Carpenter, THE DEVELOPMENT OF STRATEGIES FOR CONSTRUCTION OF THE AZIRIDINE CORE OF THE ANTITUMOR AGENTS AZINOMYCIN-A AND AZINOMYCIN-B, Tetrahedron, 53(48), 1997, pp. 16313-16326
Citations number
46
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
48
Year of publication
1997
Pages
16313 - 16326
Database
ISI
SICI code
0040-4020(1997)53:48<16313:TDOSFC>2.0.ZU;2-8
Abstract
The synthesis of the C6-C13 aziridino[1,2a]pyrrolidine core substructu re of the antitumor agents azinomycins A (1a) and B (1b) is described. Key synthetic steps included Wadsworth-Horner-Emmons olefination for formation of the C7-C8 double bond, an E-selective electrophilic bromi nation of the C8 position, and a stereospecific intramolecular additio n-elimination reaction sequence for formation of the N-C8 pyrrolidine bond. (C) 1997 Elsevier Science Ltd.