- Synthesis of (+)- and (-)-ferruginol via asymmetric cyclization of a polyene
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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.
- Tada, Masahiro,Nishiiri, Sei,Zhixiang, Yang,Imai, Yumiko,Tajima, Shiho,Okazaki, Naoko,Kitano, Yoshikazu,Chiba, Kazuhiro
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p. 2657 - 2664
(2007/10/03)
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- Stereoselective synthesis of (+)-ferruginyl methyl ether and (+)-sugiyl methyl ether
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A facile stereoselective synthetic procedure to (+)-ferruginyl methyl ether and (+)-sugiyl methyl ether has been developed with high stereoselectivity and overall yield.
- Yonghong, Gan,Xinfu, Pan
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p. 130 - 132
(2007/10/03)
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- Stereoselective synthesis of (-)-6,7-dehydroferruginyl methyl ether
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A stereoselective synthetic route to (-)-6,7-dehydroferruginyl methyl ether was developed from (S)-(-)-α-cyclocitral. Copyright (C) 2000 Elsevier Science Ltd.
- Gan, Yonghong,Li, Anpai,Pan, Xinfu,Chan, Albert S. C.,Yang, Teng-Kuei
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p. 781 - 787
(2007/10/03)
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