NEW DIHYDRO AND TETRAHYDRO DERIVATIVES OF DESMYCOSIN .3. THE OPENING OF OXIRANE RING OF 12,13-EPOXYDESMYCOSIN

Authors
NARANDA A LOPOTAR N KELNERIC Z
Citation
A. Naranda et al., NEW DIHYDRO AND TETRAHYDRO DERIVATIVES OF DESMYCOSIN .3. THE OPENING OF OXIRANE RING OF 12,13-EPOXYDESMYCOSIN, Journal of antibiotics, 50(10), 1997, pp. 860-865
Citations number
12
Categorie Soggetti
Pharmacology & Pharmacy",Immunology,"Biothechnology & Applied Migrobiology
Journal title
Journal of antibiotics → ACNP
ISSN journal
00218820
Volume
50
Issue
10
Year of publication
1997
Pages
860 - 865
Database
ISI
SICI code
0021-8820(1997)50:10<860:NDATDO>2.0.ZU;2-X
Abstract
Opening the oxirane ring of 12,13-epoxydesmycosin dimethylacetal (1) b y catalytic hydrogenation gave the 10,11-dihydro-12,13-epoxy derivativ e (3) as the main product. Reductive oxirane cleavage was accomplished with dissolved metal (Zn) giving the 10,13-dihydro-13-hydroxy compoun d (6). Mild acid hydrolysis of 6 gave expected 10,13-dihydro-13-hydrox ydesmycosin (8), but hydrolysis of 3, under the same conditions, gave three tautomeric desepoxy products.