Synthesis of Six-Membered Compounds by Environmentally Friendly Cyclization Using Indirect Electrolysis

[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 tac...

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Veröffentlicht in:Journal of organic chemistry 1996-01, Vol.61 (2), p.677-684
Hauptverfasser: Ihara, Masataka, Katsumata, Akira, Setsu, Fumihito, Tokunaga, Yuji, Fukumoto, Keiichiro
Format: Artikel
Sprache:eng
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Zusammenfassung:[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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo951653e