SYNTHESIS OF 6-MEMBERED COMPOUNDS BY ENVIRONMENTALLY FRIENDLY CYCLIZATION USING INDIRECT ELECTROLYSIS

Citation
M. Ihara et al., SYNTHESIS OF 6-MEMBERED COMPOUNDS BY ENVIRONMENTALLY FRIENDLY CYCLIZATION USING INDIRECT ELECTROLYSIS, Journal of organic chemistry, 61(2), 1996, pp. 677-684
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
00223263
Volume
61
Issue
2
Year of publication
1996
Pages
677 - 684
Database
ISI
SICI code
0022-3263(1996)61:2<677:SO6CBE>2.0.ZU;2-G
Abstract
[Ni(cyclam)](ClO4)(2)-catalyzed indirect electroreduction of olefinic bromides produced six-membered compounds in low to high yields. The sy nthetic intermediate 49 of Ipecac and Corynanthe alkaloids was obtaine d in 88% yield in a highly stereoselective manner. Lactam 66, the synt hetic precursor of tacamonine, was prepared in 49% yield as a mixture of two diastereoisomers. The electrolysis of the bromoacetates gave th e debrominated compounds in good yields.