A Convenient Enantiospecific Route towards Bioactive Merosesquiterpenes by Cationic-Resin-Promoted Friedel-Crafts Alkylation with α,β-Enones
A Convenient Enantiospecific Route towards Bioactive Merosesquiterpenes by Cationic-Resin-Promoted Friedel-Crafts Alkylation with α,β-Enones
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DOI：
10.1002/ejoc.200801174
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发表时间：
2009-03-01
影响因子：
2.8
通讯作者：
Barranco, Inmaculada
中科院分区：
文献类型：
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作者：
Alvarez-Manzaneda, Enrique;Chahboun, Rachid;Barranco, Inmaculada
报道了一种基于阳离子树脂促进的烷氧基芳烃与α，β-不饱和酮的Friedel-Crafts烷基化反应的对映体特异性路线。酮11与3，4-亚甲二氧基苯酚反应得到相应的色烯。用保护的苯酚20处理11得到芳基去甲氢吡喃酮21，其是合成生物活性的部分倍半萜及其8-表衍生物的合适中间体。通过利用这种方法，描述了通过三氟甲磺酸酯25的（+）-普乌哌酮和其他相关代谢物的正式合成。((C)Wiley-VCH Verlag GmbH & Co. KGaA，69451魏因海姆，德国，2009）
An enantiospecific route towards bioactive merosesquiterpenes, based on the cationic-resin-promoted Friedel-Crafts alkylation of alkoxyarenes with an alpha,beta-unsaturated ketone, is reported. Reaction of ketone 11 with 3,4-methylenedioxyphenol afforded the corresponding chromene. Treatment of 11 with protected phenol 20 gave aryl nordrimane ketone 21, a suitable intermediate in the synthesis of bioactive merosesquiterpenes and their 8-epi derivatives. By utilizing this methodology, a formal synthesis of (+)-puupehenone and other related metabolites, via triflate 25, is described. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)