Synthesis of six-membered compounds by environmentally friendly cyclization using indirect electrolysis

被引:62
作者
Ihara, M [1 ]
Katsumata, A [1 ]
Setsu, F [1 ]
Tokunaga, Y [1 ]
Fukumoto, K [1 ]
机构
[1] TOHOKU UNIV,INST PHARMACEUT,SENDAI,MIYAGI 98077,JAPAN
关键词
D O I
10.1021/jo951653e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[Ni(cyclam)](ClO4)(2)-catalyzed indirect electroreduction of olefinic bromides produced six-membered compounds in low to high yields. The synthetic intermediate 49 of Ipecac and Corynanthe alkaloids was obtained in 88% yield in a highly stereoselective manner. Lactam 66, the synthetic precursor of tacamonine, was prepared in 49% yield as a mixture of two diastereoisomers. The electrolysis of the bromoacetates gave the debrominated compounds in good yields.
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页码:677 / 684
页数:8
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