학술논문
2-substituted 2,3-dihydro-4H-1,3-benzoxazin-4-ones: novel auxiliaries for stereoselective synthesis of 1-beta-methylcarbapenems
Document Type
Academic Journal
Source
Journal of Organic Chemistry. May 2, 1997, Vol. 62 Issue 9, p2877, 8 p.
Subject
Language
ISSN
0022-3263
Abstract
A stereoselective synthetic strategy for the construction of the 1-beta-methylcarbapenem nucleus was developed based on Reformatsky-type reactions. The synthetic approach was characterized by the formation of a 1-beta-methylcarbapenem intermediate from a dihydrobenzoxazone that was derived from salicylamide and cyclohexanone. Zinc-induced Reformatsky-type reactions involving the achiral 2-substituted dihydrobenzoxanones also led to the formation of acetoxyazetidinone and the desired 1-beta-methylcarbapenems.