Concise, stereoselective approach to the spirooxindole ring system of citrinadin A

Concise, stereoselective approach to the spirooxindole ring system of citrinadin A
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DOI:
10.1021/ol702132v
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发表时间:
2007-10-25
期刊:
影响因子:
5.2
通讯作者:
Martin, Stephen F.
Martin, Stephen F.
中科院分区:
化学1区
文献类型:
--
作者:
Pettersson, Martin;Knueppel, Daniel;Martin, Stephen F.

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合成了柑桔苷A的螺旋吲哚环体系,对螺中心的绝对立体化学控制良好。关键步骤涉及在吲哚氮上使用8-苯基薄荷醇手性助剂的新型非对映选择性ddo介导的氧化重排。
The spirooxindole ring system of citrinadin A has been synthesized with excellent control over the absolute stereochemistry at the spirocenter. The key step involves a novel diastereoselective DMDO-mediated oxidative rearrangement employing an 8-phenylmenthol chiral auxiliary on the indole nitrogen.