Total Synthesis of (-)-Anisatin

Total Synthesis of (-)-Anisatin
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DOI:
10.1021/ol300390k
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发表时间:
2012-03-16
期刊:
影响因子:
5.2
通讯作者:
Fukuyama, Tohru
Fukuyama, Tohru
中科院分区:
化学1区
文献类型:
--
作者:
Ogura, Akihiro;Yamada, Kohei;Fukuyama, Tohru

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开发了一条合成(-)-茴香素的新路线。我们的合成具有如下特点:1,4-芳基硼酸的铑催化加成,邻苯二酮单缩酮的分子内Diels Alder反应,立体选择性的[2,3]-Wittig重排,以及通过伯胺裂解环氧化物来构建氧双环[3.3.1]骨架。
A novel synthetic route to (-)-anisatin has been developed. Our synthesis features a rhodium-catalyzed 1,4-addition of an arylboronic acid, an intramolecular Diels Alder reaction of an ortho-quinone monoketal, a stereoselective [2,3]-Wittig rearrangement, and construction of the oxabicyclo [3.3.1] skeleton via cleavage of an epoxide by a primary amide.