
Journal of Organic Chemistry p. 4862 - 4867 (1994)
Update date:2022-07-30
Topics:
Guzzo, Peter R.
Miller, Marvin J.
A catalytic, asymmetric synthesis of the carbacephem β-lactam framework is reported.The initial asymmetric center was established by catalytic hydrogenation of β-keto ester 12 with (S)-Ru-BINAP.The β-lactam ring was prepared using the hydroxamate approach (14 -> 15).The nitrogen substituent at C7 was introduced by the nucleophile transfer reaction (15 -> 17), and the six-membered ring of the carbacephem was prepared by a directed Dieckmann condensation (24 -> 25).
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Doi:10.1021/om5000908
(2014)Doi:10.1039/DT9940002339
(1994)Doi:10.1021/bc400486w
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