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Synthetic Studies on Tricyclic Diterpenoids: Direct Allylic Amination Reaction of Isopimaric Acid Derivatives
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نویسنده
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timoshenko m.a. ,kharitonov y.v. ,shakirov m.m. ,bagryanskaya i.y. ,shults e.e.
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منبع
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chemistryopen - 2016 - دوره : 5 - شماره : 1 - صفحه:65 -70
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چکیده
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A selective synthesis of 7-or 14-nitrogen containing tricyclic diterpenoids was completed according to a strategy in which the key step was the catalyzed direct allylic amination of methyl 14α-hydroxy-15,16-dihydroisopimarate with a wide variety of nitrogenated nucleophiles. it was revealed that the selectivity of the reaction depends on the nature of nucleophile. the catalyzed reaction of the mentioned diterpenoid allylic alcohol with 3-nitroaniline,3-(trifluoromethyl)aniline,and 4-(trifluoromethyl)aniline yield the subsequent 7α-,7β-and 14αnitrogen-containing diterpenoids. the reaction with 2-nitroaniline,4-nitro-2-chloroaniline,4-methoxy-2-nitroaniline,phenylsulfamide,or tert-butyl carbamate proceeds with the formation of 7α-nitrogen-substituted diterpenoids as the main products. © 2015 the authors. published by wiley-vch verlag gmbh & co. kgaa. weinheim.
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کلیدواژه
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allylic amination reaction; diterpenoids; gold catalysis; pimaranes; stereoselectivity
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آدرس
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laboratory of medicinal chemistry,novosibirsk institute of organic chemistry,siberian branch,russian academy of sciences,lavrentyev avenue,9,novosibirsk,630090,russian federation,chemical and physical departments,novosibirsk state university,pirogova st. 2,novosibirsk,630090, Russian Federation, laboratory of medicinal chemistry,novosibirsk institute of organic chemistry,siberian branch,russian academy of sciences,lavrentyev avenue,9,novosibirsk,630090,russian federation,chemical and physical departments,novosibirsk state university,pirogova st. 2,novosibirsk,630090, Russian Federation, laboratory of medicinal chemistry,novosibirsk institute of organic chemistry,siberian branch,russian academy of sciences,lavrentyev avenue,9,novosibirsk,630090, Russian Federation, laboratory of medicinal chemistry,novosibirsk institute of organic chemistry,siberian branch,russian academy of sciences,lavrentyev avenue,9,novosibirsk,630090,russian federation,chemical and physical departments,novosibirsk state university,pirogova st. 2,novosibirsk,630090, Russian Federation, laboratory of medicinal chemistry,novosibirsk institute of organic chemistry,siberian branch,russian academy of sciences,lavrentyev avenue,9,novosibirsk,630090,russian federation,chemical and physical departments,novosibirsk state university,pirogova st. 2,novosibirsk,630090, Russian Federation
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Authors
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