121703-00-2Relevant articles and documents
Synthesis of (+)- and (-)-ferruginol via asymmetric cyclization of a polyene
Tada, Masahiro,Nishiiri, Sei,Zhixiang, Yang,Imai, Yumiko,Tajima, Shiho,Okazaki, Naoko,Kitano, Yoshikazu,Chiba, Kazuhiro
, p. 2657 - 2664 (2000)
Stereoselectivity of modified polyenes which have a terminal benzene ring was found to be dependent on the size of substituent on the adjacent asymmetric carbon to the terminal benzene ring of the polyenes. (R)-(+)-2′-Hydroxy-1,1′-binaphthyl-2-yl(2R)-2-(4-methoxyphenyl)-5,9- dimethyldeca-4,8-dienoate gave(R)-(+)-2′-hydroxy-1,1′-binaphthyl-2-yl (4aS,9 R, 10aS)-1,2,3,4,4a,9,10,10a-octahydro-6-methoxy-1,1,4a-trimethylphenanthene-9- carboxylate stereoselectively by treatment with BF3-Et2O in nitromethane. The products were elaborated to (+)-ferruginol 1. (-)-Ferruginol 2 and (±)-ferruginol 3 were also synthesized via a similar synthetic route. The Royal Society of Chemistry 2000.
