Highly Stereocontrolled Synthesis Of The Key Intermediate Of 1-Beta-Methylcarbapenem Antibiotic Via Intramolecular Nitrone 1,3-Dipolar Cyclo-Addition

M Ihara,M Takahashi, K Fukumoto,T Kametani

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS（1988）

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摘要

The key synthetic intermediate of 1β-methylcarbapenem antibiotic, (–)-(3S, 4R)-3-[(1R)-1-t- butyl-dimethylsiloxyethyl]-4-[(2R)-2-(1-hydroxypropyl)]azetidin-2-one (2), was synthesised from (R)-methyl 3-hydroxy-2-methylpropionate with high stereoselectivity via intramolecular nitrone 1,3-dipolar cycloaddition.

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