Syntheses based on 1,2-secopenicillins. Part II. Preparation of 4-(3-substituted prop-2-ynylthio)azetidin-2-ones
Abstract
Treatment of benzyl 6β-(triphenylmethylamino)penicillanate with 3-substituted prop-2-ynyl bromides in the presence of strong base gave 1,2-secopenicillanates, which on permanganate oxidation afforded (3R,4R)-4-(3-substituted prop-2-ynylthio)-3-(triphenylmethylamino)azetidin-2-ones.