Total synthesis of (±)-herbindole (±)-cis-trikentrin B

被引：75

作者：

Jackson, SK ^{[1
]}

Banfield, SC ^{[1
]}

Kerr, MA ^{[1
]}

机构：

[1] Univ Western Ontario, Dept Chem, London, ON N6A 5B7, Canada

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 07期

关键词：

D O I：

10.1021/ol047498k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herbindole B and cis-trikentrin B are naturally occurring indoles having the unusual and synthetically challenging pattern of carbon substitution at the 4-7 and 5-7 positions, respectively, with no substitution at the 1-3 positions. The total syntheses of these polyalkylated indoles have been achieved in 19 and 12 steps, respectively. The synthesis of herbindole B relies on two iterations of a quinine monoimine Diels-Alder reaction, while cis-trikentrin B uses a single cycloaddition of a suitable quinone monolmine. Indolization of the adducts provides suitably substituted benzopyrrole nuclei for elaboration to the natural products.

引用

页码：1215 / 1218

页数：4

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