High Pressure Diels-Alder Approach to Hydroxy-Substituted 6a-Cyano-tetrahydro-6H-benzo[c]chromen-6-ones: A Route to Δ6-Cis-Cannabidiol
High Pressure Diels-Alder Approach to Hydroxy-Substituted 6a-Cyano-tetrahydro-6H-benzo[c]chromen-6-ones: A Route to Δ6-Cis-Cannabidiol
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DOI：
10.1021/jo9005365
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发表时间：
2009-06-05
影响因子：
3.6
通讯作者：
Pizzo, Ferdinando
中科院分区：
文献类型：
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作者：
Ballerini, Eleonora;Minuti, Lucio;Pizzo, Ferdinando
报道了3-氰基香豆素、羟基取代的3-氰基香豆素和甲磺酰基取代的3-氰基香豆素与甲基丁二烯在高压（11 kbar）下的Diels-Alder环加成反应。通过高压活化使得这些反应在温和条件下令人满意地进行，以中等至优异的产率产生6 α-氰基-羟基-和6 α-氰基-甲磺酰基-四氢-6H-苯并[c]色烯-6-酮。介绍了δ（6）-3，4-顺式大麻二酚（Delta（6）-cis-CBD）和δ（8）-cis-tetrahydrocannabinol（Delta（8）-cis-THC）的前体化合物cis-1-羟基-9-甲基-3-戊基-6a，7，10，10a-四氢苯并[c]色烯-6-酮的合成。
Diels-Alder cycloaddition reactions of 3-cyanocoumarin, hydroxy-substituted 3-cyanocoumarins and mesyl-substituted 3-cyano-coumarins with methyl-1,3-butadienes carried out under high pressure (11 kbar) are reported. Activation by high pressure allows these reactions to proceed satisfactorily under mild conditions to produce 6a-cyano-hydroxy- and 6a-cyano-mesyl-tetrahydro-6H-benzo[c]chromen-6-ones in moderate to excellent yield. The synthesis of cis-1-hydroxy-9-methyl-3-pentyl-6a,7, 10,10a-tetrahydro-benzo[c]chromen-6-one as precursor of Delta(6)-3,4-cis-cannabidiol (Delta(6)-cis-CBD) and Delta(8)-cis-tetrahydrocannabinol (Delta(8)-cis-THC) is outlined.