SYNTHESIS OF 5'-(2H3)-(-)-11-NOR-9-CARBOXY-DELTA-9-TETRAHYDROCANNABINOL METHYL-ESTER METHYL-ETHER
SYNTHESIS OF 5'-(2H3)-(-)-11-NOR-9-CARBOXY-DELTA-9-TETRAHYDROCANNABINOL METHYL-ESTER METHYL-ETHER
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DOI：
10.1016/s0040-4020(01)85608-8
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发表时间：
1992-10-16
期刊：
影响因子：
2.1
通讯作者：
KANNANGARA, GSK
中科院分区：
文献类型：
--
作者：
TIUS, MA;KANNANGARA, GSK
以-溴烯酮10为原料合成了5'-(H-2(3))-(-)-11-不-9-羧基- delta9 -四氢大麻酚甲酯甲基醚(4)。关键步骤是铜酸酯加合物18的立体控制环丁烷开环和三氟化环己烯酯21与过量碘三甲基硅烷环化生成delta9 -三氟化环己烯酯22。光学活性(-)-11-no -9-酮-六氢大麻酚(8)的高效立体特异性合成也已完成。
A synthesis of 5'-(H-2(3))-(-)-11-nor-9-carboxy-DELTA9-tetrahydrocannabinol methyl ester methyl ether (4) has been accomplished from alpha-bromoenone 10. The key steps are the stereocontrolled cyclobutane ring opening of the cuprate adduct 18 and the cyclization of the cyclohexenyl triflate 21 with excess iodotrimethylsilane to produce DELTA9-cyclohexenyl triflate 22. An efficient, stereospecific synthesis of optically active (-)-11-nor-9-keto-hexahydrocannabinol (8) has also been accomplished.