Mercuric triflate-catalyzed tandem cyclization leading to polycarbocycles.
[reaction: see text] We developed Hg(OTf)2-catalyzed cyclization of (E)-1,3-dimethoxy-5-(4-methyl-3-nonen-7-ynyl)benzene leading to the formation of (4aS,10aS)-3,4,4a,9,10,10a-hexahydro-5,7-dimethoxy-1,4a-dimethylphenanthrene in 98% yield with up to 100 catalytic turnovers. This is the first mercuric salt-catalyzed biomimetic tandem cyclization.
Imagawa
Hiroshi
H
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
Iyenaga
Tomoaki
T
Nishizawa
Mugio
M
D002384:Catalysis; D003500:Cyclization; D017669:Mercury Compounds / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D008958:Models, Molecular; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000494:pharmacology
D017669:Mercury Compounds; D008698:Mesylates; D011083:Polycyclic Compounds; C510262:mercuric triflate