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首页> 外文期刊>Chemistry: A European journal >Regioselective Bromination of Benzocycloheptadienones for the Synthesis of Substituted 3,4-Benzotropolones Including Goupiolone A
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Regioselective Bromination of Benzocycloheptadienones for the Synthesis of Substituted 3,4-Benzotropolones Including Goupiolone A

机译：苯并苯并二烷酮的区域选择性溴化素用于合成取代的3,4-苯基酮，包括亮胺A

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摘要

Type-18 or -23 benzocycloheptadienones are readily prepared by ring-closing olefin metatheses. Adding Br_2 to 23 and eliminating HBr gave the bromoolefin 28 using DBU or its isomer iso-28 using DABCO, both with near-perfect regiocontrol. Both 28 and iso-28 underwent Sonogashira, Suzuki, Negishi, and Heck couplings as well as Pd-catalyzed alkoxycarbonylations. Hydrolysis of the resulting α-ketoketals and enolization of the liberated a-diketones delivered a portfolio of hitherto unknown 3,4- benzotropolones. The 8-ethoxycarbonylated dimethyl-3,4- benzotropolone 50 obtained by this route was dimethylated to give goupiolone A (52). This synthesis encompasses 9 steps from 22, that is, half as many as the only previous synthesis (19 steps). A variant of our route afforded the 1,8-dibromide 54. Coupling with excess phenylboronic acid and ketal hydrolysis provided the diphenylated benzotropolone 56 and suggests a strategy, by which the natural bispulvinone aurantricholone (7) might be reached.
机译：18型或-23苯并苯脲己酮通过环闭烯烃元分离易于制备。添加BR_2至23并消除HBR使用DABCO使用DBU或其异构体ISO-28使用DABCO，包括近乎完美的Regiocontrol。 28和ISO-28经过Sonogashira，Suzuki，Negishi和Heck偶联以及PD催化的烷氧基羰基化。所得α-酮酮的水解和释放的a-diketone的雄化赋予迄今未知的3,4-苯并克罗克罗克罗克罗克罗克罗克罗克罗克隆的组合。通过该途径获得的8-乙氧基羰基化的二甲基-3,4-苯并泊孔50离甲基化以得到胶​​醇A（52）。该合成包括来自22的9步，即，与之前的唯一合成（19步）一样多。我们的途径的变体提供了1,8-二溴化物54.与过量的苯基硼酸和缩酮水解的偶联提供了双苯基化苯并棒56，并提出了一种策略，可以达到天然Bispulvinone Aurantro酮（7）。

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