Stereoselective furan-iminium cation cyclization in the construction of the core structure of manzamine A.
[reaction: see text] A new type of furan-iminium cation cyclization was developed and used to construct the ABC ring of manzamine A. The cyclization proceeded at the 2-position with complete regio- and stereoselectivity to give a spiro-center. The product was efficiently converted to the highly substituted core structure of manzamine A.
Tokumaru
Kazuyuki
K
Graduate School of Pharmaceutical Sciences, Chiba University, Yayoi-cho, Inage-ku, Japan.
Arai
Shigeru
S
Nishida
Atsushi
A
D002227:Carbazoles; D002412:Cations; D003500:Cyclization; D005663:Furans / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D008958:Models, Molecular; D011758:Pyrroles / Q000737:chemistry*; D013237:Stereoisomerism; D014961:X-Ray Diffraction
D002227:Carbazoles; D002412:Cations; D005663:Furans; D007097:Imines; D007211:Indoles; D011758:Pyrroles; C078290:manzamine A