A new and general synthetic pathway to Strychnos indole alkaloids:: Total syntheses of (-)-dehydrotubifoline and (-)-tubifoline by palladium-catalyzed asymmetric allylic substitution

被引：37

作者：

Mori, M ^{[1
]}

Nakanishi, M ^{[1
]}

Kajishima, D ^{[1
]}

Sato, Y ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 12期

关键词：

D O I：

10.1021/ol0159571

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A novel procedure for the synthesis of an indole skeleton was developed, Treatment of a cyclohexenol derivative having a silyloxymethyl group at the 2-position with N-tosyl-o-bromoaniline in the presence of Pd(2)dba(3). CHCl3 and (S)-BINAPO gave compound 6a with 84% ee in 75% yield, Compound 6a was converted into 11, which was treated with Pd(OAc)(2) and Me2PPh in the presence of Ag2CO3 to give indoline derivative 12, From 12, we succeeded in the total syntheses of (-).dehydrotubifoline and (-).tubifoline.

引用

页码：1913 / 1916

页数：4

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