Synthesis of Six-Membered Compounds by Environmentally Friendly Cyclization Using Indirect Electrolysis.
[Ni(cyclam)](ClO(4))(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.
Ihara
Masataka
M
Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-77, Japan.
Katsumata
Akira
A
Setsu
Fumihito
F
Tokunaga
Yuji
Y
Fukumoto
Keiichiro
K