The Journal of Organic Chemistry

The synthesis of substituted [[3 (S)-(acylamino)-2-oxo-1-azetidinyl] thio] acetic acids

SR Woulfe, MJ Miller

Index: Woulfe, Steven R.; Miller, Marvin J. Journal of Organic Chemistry, 1986 , vol. 51, # 16 p. 3133 - 3139

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Citation Number: 53

Abstract

I the tert-butyldimethylsilyl-protectedll threonine 8 to the corresponding acid chloride (oxalyl chloride/DMF) 12 followed by reaction with triphenylmethanesufenamide 9b provided the desired thiohydroxamate 10. Unfortunately, removal of the silyl protecting group (n-Bu, NF) to provide 11 followed by attempted cyclization under modified Mitsunobu conditions (Ph3P/CC14/Et3N) did not provide any of the desired 0-lactam 13.13 In contrast, the O- ...