Vinyl quinones as Diels-Alder dienes: Concise synthesis of (-)-halenaquinone

Vinyl quinones as Diels-Alder dienes: Concise synthesis of (-)-halenaquinone
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DOI:
10.1021/ja8035042
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发表时间:
2008-07-09
影响因子:
15
通讯作者:
Trauner, Dirk
Trauner, Dirk
中科院分区:
化学1区
文献类型:
--
作者:
Kienzler, Michael A.;Suseno, Sandy;Trauner, Dirk

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介绍了一种简洁的不对称合成(-)-萘醌的方法。该合成具有非对映选择性Heck环化以设置一个季中心以及涉及乙烯醌的新型分子内逆电按需Diels-Alder反应I。该合成是高度收敛的,并且具有最小数量的保护组操作。
A concise asymmetric synthesis of (-)-halenaquinone is described. The synthesis features a diastereoselective Heck cyclization to set a quaternary center as well as a novel intramolecular inverse-electron-demand Diels-Alder reaction I involving a vinyl quinone. The synthesis is highly convergent and features a minimal amount of protecting group manipulations.