Chiral amino alcohols as intermediates in the stereocontrolled synthesis of 1,3-disubstituted tetrahydroisoquinolines and protoberberines

被引：38

作者：

Carrillo, L ^{[1
]}

Badía, D ^{[1
]}

Domínguez, E ^{[1
]}

Anakabe, E ^{[1
]}

Osante, I ^{[1
]}

Tellitu, I ^{[1
]}

Vicario, JL ^{[1
]}

机构：

[1] Univ Basque Country, Fac Ciencias, Dept Quim Organ, Bilbao 48080, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 04期

关键词：

D O I：

10.1021/jo981326h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient stereocontrolled synthetic approach to (3S)-3-aryltetrahydroisoquinoline Sd and (1S,3S)-3-aryl-1-methyltetrahydroisoquinolines 3a-c by a Pictet-Spengler heterocyclization reaction of optically active (95% ee) (S)-1,2-diarylethylamines 2a-c is presented. An alternative route toward obtaining the epimeric derivative of 3a, tetrahydroisoquinoline (1R,3S)-6, was also achieved by a stereocontrolled ring opening process carried out on the oxazolotetrahydroisoquinoline 9. Tetrahydroisoquinoline 8 was employed for the stereoselective preparation of(5S,6S, 14S)-6-phenyl-2,3,10,11-tetramethoxyprotoberberin-5-ol (12), a new type of 5,6-disubstituted protoberberine derivative with excellent (d.e>95% by H-1 NMR) stereoselection.

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页码：1115 / 1120

页数：6

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