Double cyclization of aminophosphonoacetate derived β- hydroxyacids to bicyclic β-lactams
1990; Elsevier BV; Volume: 46; Issue: 24 Linguagem: Inglês
10.1016/s0040-4020(01)81463-0
ISSN1464-5416
AutoresNai Zheng Huang, Vincent J. Kalish, Marvin J. Miller,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoThe carbon framework for carbapenems was constructed by an asymmetric aldol condensation and subsequent direct coupling of the resulting β-hydroxy acid equivalent with an aminophosphonoacetate. Cyclization to the monocyclic β-lactam 20 was followed by oxidative elaboration to the penultimate aldehyde 22 which was converted to carbapenem 23 by an intramolecular version of a Horner-Emmons cyclization.
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