Concise Total Synthesis of (±)-cis-Trikentrin A and (±)-Herbindole A via Intermolecular Indole Aryne Cycloaddition

被引:80
作者
Buszek, Keith R. [1 ,2 ]
Brown, Neil [2 ]
Luo, Diheng [2 ]
机构
[1] Univ Missouri, Dept Chem, Kansas City, MO 64110 USA
[2] Kansas State Univ, Dept Chem, Manhattan, KS 66506 USA
基金
美国国家卫生研究院;
关键词
VINYL GRIGNARD-REAGENTS; ABSOLUTE STRUCTURES; TRANS-TRIKENTRIN; (6R; 8R)-ISO-TRANS-TRIKENTRIN-B; 8R)-TRANS-TRIKENTRIN-B; 8S)-CIS-TRIKENTRIN-B; NITROARENES; REACTIVITY; TELEOCIDIN; SPONGE;
D O I
10.1021/ol802425m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient nine-step total synthesis of the annulated Indole natural products (+/-)-cis-trikentrin A and (+/-)-herbindole A was accomplished via an Intermolecular Diels-Alder cycloaddition using our recently developed Indole aryne (indolyne) methodology as the key step. This strategy provides rapid access into the trikentrins and the related herbindoles and represents the first application of this methodology to natural products total synthesis. The required 6,7-Indolyne precursor was readily constructed by means of the Bartoli indole synthesis with substituted nitrobenzenes and vinyl magnesium bromide.
引用
收藏
页码:201 / 204
页数:4
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