Activation by Charcoal by Bancroft W. D.

By Bancroft W. D.

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2 Biological Evaluation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 89 4 Concluding Remarks . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 95 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

2 Using Radical Reactions The reductive opening of epoxy-b-lactam 97 with titanocene(III) chloride gives rise to a benzyl radical that can be trapped by intramolecular p systems to give the tricyclic 2-azetidinone 98 (Scheme 32) [78]. An approach (racemic and asymmetric) to benzofused tricyclic b-lactams including benzocarbapenems as well as benzocarbacephems, through intramolecular aryl radical cyclization of 2-azetidinone-tethered haloarenes has been reported [79]. Haloaryl b-lactams 99–103 were reacted with tributyltin hydride and AIBN in benzene at reflux to give the expected benzocarbapenems 104 and 106 and benzocarbacephems 105, 107, and 108 in good yields as single diastereomers after chromatographic purification (Scheme 33, Table 1).

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