Synthesis of (+)- and (−)-ferruginol via asymmetric cyclization of a polyene
Synthesis of (+)- and (−)-ferruginol via asymmetric cyclization of a polyene
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DOI：
10.1039/b003497p
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发表时间：
2000
期刊：
影响因子：
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通讯作者：
M. Tada;Sei Nishiiri;Zhixiang Yang;Y. Imai;S. Tajima;N. Okazaki;Y. Kitano;K. Chiba
中科院分区：
文献类型：
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作者：
M. Tada;Sei Nishiiri;Zhixiang Yang;Y. Imai;S. Tajima;N. Okazaki;Y. Kitano;K. Chiba
具有末端苯环的改性多烯的立体选择性取决于其末端苯环附近的不对称碳上取代基的大小。(R)-(+)-2‘-羟基-1，1’-联萘-2-基(2R)-2-(4-methoxyphenyl)-5，9-dimethyldeca-4，8-dienoate在硝基甲烷中与BF3·Et2O反应得到(R)-(+)-2‘-羟基-1，1’-联萘-2-基(4aS，9R，10aS)-1，2，3，4，4a，9，10，10a-octahydro-6-methoxy-1，1，4a-trimethylphenanthene-9-carboxylate。通过相似的合成路线合成了(+)-铁锈醇1、(−)-铁锈醇2和(±)-铁锈醇3。
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,9R,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.