Synthesis of 2α-Methyl- and 2β-Methyl-3-(substituted methyl) cephalosporins, and 2,3-Diexomethylenecepham
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概要
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The stereoselective synthesis of 2α-methyl-and 2β-methyl-3-(substituted methyl)-cephalosporins via 2-methyl-3-formyloxymethylceph-2-em (5) and 2-methyl-3-acetoxymethylceph-2-em (16) from 2-methylene-3-acetoxymethylcephalosporin (1) is described. Reduction of 1 with zinc in acetic acid gave 2,3-dimethylenecepham (2), while reduction with zinc in formic acid gave 5 and reduction with sodium borohydride gave 16. Hydrolysis of 5 gave 2-methyl-3-hydroxymethylceph-2-em (6), which was stereoselectively converted via 2-methyl-3-(heterocyclic thiomethyl) ceph-2-em (8) and 2-methyl-3-formyl-ceph-2-em (12) into the corresponding 2α-methyl-3-(substituted methyl) ceph-3-ems by oxidation with peracid. On the other hand, isomerization of 16 to the corresponding ceph-3-em by oxidation with peracid gave mainly the 2β-methyl isomer (55 : 1 ratio). Ozonolysis of 2 followed by treatment with diazomethane gave 2-oxo-3-methoxyceph-3-em (24).
- 公益社団法人日本薬学会の論文
- 1983-05-25
著者
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溝上 業彬
Central Research Division Takeda Chemical Industries Ltd.
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桑田 胖
Central Research Division, Takeda Chemical Industries, Ltd.
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堀井 聰
Central Research Division Takeda Chemical Industries Ltd.
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深瀬 泱
Central Research Division, Takeda Chemical Industries, Ltd.
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深瀬 泱
Central Research Division Takeda Chemical Industries Ltd.
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桑田 胖
Central Research Division Takeda Chemical Industries Ltd.
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