Regiocontrol in MnIII-mediated oxidative heterobicyclizations:: Access to the core skeletons of oroidin dimers

被引:61
作者
Tan, Xianghui [1 ]
Chen, Chuo [1 ]
机构
[1] Univ Texas, Dept Biochem, SW Med Ctr Dallas, Dallas, TX 75390 USA
关键词
cascade reactions; natural products; radical reactions; rearrangement; synthetic methods;
D O I
10.1002/anie.200601208
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) In control: A cyclization reaction of an allylic β-imidazolinonyl-β-ketoester 1 is carried out in a Mn III-promoted radical cascade. The reaction pathway (5-exo/6-endo or 5-exo/5-exo) can be directed to construct the central cyclopentyl and cyclohexenyl core skeletons (2 and 3) of two classes of oroidin dimers with regiocontrol. An oxidative rearrangement can also be used to convert 2 into 3. PG = protecting group. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4345 / 4348
页数:4
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