STEREOCONTROLLED FORMATION OF EPOXIDES ON TO THE RING A OF DAUNORUBICINONE DERIVATIVES

Authors
GUIDI A CANFARINI F PASQUI F PESTELLINI V TRIOLO A ARCAMONE F
Citation
A. Guidi et al., STEREOCONTROLLED FORMATION OF EPOXIDES ON TO THE RING A OF DAUNORUBICINONE DERIVATIVES, Anales de quimica, 91(3-4), 1995, pp. 236-239
Citations number
11
Categorie Soggetti
Chemistry
Journal title
Anales de quimica → ACNP
ISSN journal
11302283
Volume
91
Issue
3-4
Year of publication
1995
Pages
236 - 239
Database
ISI
SICI code
1130-2283(1995)91:3-4<236:SFOEOT>2.0.ZU;2-5
Abstract
8-(S)-Hydroxydaunorbicinone-7-O-methyl ether (4) was selectively conve rted into either (8R, 9S)-9-deoxy-8,9-epoxydaunorbicinone-7-O (3), or 8S,9R isomeric epoxide (5). The fatter compound resulted from an unexp ected DAST [(diethylamino)sulfur trifluoride] induced dehydration of t he starting material. Mechanistic implications and considerations for further elaboration of ring A in daunorubicin are discussed.