β-Lactam antifungals. II. Enantiocontrolled synthesis of (2R,5S)-2-hydroxymethyl-1-carbapenam, the carba-analog of a clavam antifungal

DOI: 10.1248/cpb.39.2813

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 2813 - 2818 (1991)

Update date:2022-07-30

Topics:

Authors:

Konosu Konosu

Furukawa

Hata Hata

Oida Oida

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Article abstract of DOI:10.1248/cpb.39.2813

(2R,5S)-2-Hydroxymethyl-1-carbapenam (3), the carba-analog of an antifungal β-lactam (2R,5S)-2-(hydroxymethyl)clavam (1), was synthesized in an enantiocontrolled manner, starting from the coupling reaction of an optically active phthalimido-acetate (3S,4S)-4 and an allylsilane 7, followed by removal of the phthalimido group that was crucial for asymmetric induction. Hydroboration, protecting-group interconversion, and cyclization gave 3 stereoselectively.

Full text of DOI:10.1248/cpb.39.2813

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