Heterocyclic Prostaglandins. VI. Synthesis of 11-Deoxy-8,10-diazaprostaglandin E_1 and Its 10-Methyl Derivative
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概要
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The synthesis of 11-deoxy-8,10-diazaprostaglandin E_1 (1a) starting from methyl 3-benzyloxycarbonyl-2-oxo-4-imidazolidinecarboxylate (3a) is reported. Alkylation of 3a with methyl 7-bromoheptanoate and NaH gave methyl 1-benzyloxycarbonyl-3-(6-methoxycarbonyl) hexyl-2-oxo-4-imidazolidinecarboxylate (9), which was converted into the 4-hydroxymethyl-imidazolidine derivative (10). The Moffatt oxidation of 10,and the Wittig reaction of the resulting aldehyde (11) with dimethyl 2-oxoheptylphosphonate provided an enone (12). Reduction of 12,and hydrolysis of a mixture of C_<15>-epimeric alcohols (15) followed by re-esterification afforded 11-deoxy-8,10-diazaprostaglandin E_1 methyl ester (17a). Alkaline hydrolysis of 17a gave 1a as crystals in a good yield. The 10-methyl derivative (2a) was also synthesized. Methylation of 3a with methyl iodide and K_2CO_3 gave the 1-methylimidazolidine analog (7a), which was converted into methyl 3-(6-methoxycarbonyl) hexyl-1-methyl-2-oxo-4-imidazolidinecarboxylate (20) after debenzyloxycarbonylation and alkylation with methyl 7-bromoheptanoate. Conversion of 20 into 2a was carried out by a synthetic sequence similar to that used for the elaboration of 1a.
- 社団法人日本薬学会の論文
- 1980-05-25
著者
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石田 昭彦
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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西条 成良
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.
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和田 征夫
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.
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日水 順一
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.
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和田 征夫
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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日水 順一
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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