DEHYDROAMINO ACID-DERIVATIVES FROM D-ARABINOSE AND L-SERINE - SYNTHESIS OF MODELS FOR THE AZINOMYCIN ANTITUMOR ANTIBIOTICS

Authors
MORAN EJ TELLEW JE ZHAO ZC ARMSTRONG RW
Citation
Ej. Moran et al., DEHYDROAMINO ACID-DERIVATIVES FROM D-ARABINOSE AND L-SERINE - SYNTHESIS OF MODELS FOR THE AZINOMYCIN ANTITUMOR ANTIBIOTICS, Journal of organic chemistry, 58(27), 1993, pp. 7848-7859
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
58
Issue
27
Year of publication
1993
Pages
7848 - 7859
Database
ISI
SICI code
0022-3263(1993)58:27<7848:DAFDAL>2.0.ZU;2-8
Abstract
Synthesis of aldehydes 17 from D-arabinose and 31 from L-serine provid ed key precursors for the generation of highly functionalized dehydroa mino acid derivatives upon condensation with glycyl phosphonates. Subs equent bromination and intramolecular addition/elimination afforded th e azabicyclo[3.1.0]hex-2-ylidene ring system postulated to exist in th e azinomycin antitumor antibiotics.