Asymmetric synthesis of six tetrahydroisoquinoline natural products through α-amination of an aldehyde

被引：3

作者：

Ansari, Anas ^{[1
]}

Gorde, Amol B. ^{[1
]}

Ramapanicker, Ramesh ^{[1
,2
]}

机构：

[1] Indian Inst Technol Kanpur, Dept Chem, Kanpur 208016, Uttar Pradesh, India

[2] Indian Inst Technol Kanpur, Ctr Environm Sci & Engn, Kanpur 208016, Uttar Pradesh, India

来源：

TETRAHEDRON | 2021年 / 88卷

关键词：

Aldehydes; Amination; Asymmetric synthesis; Natural products; Tetrahydroisoquinolines; C; N-CYCLIC AZOMETHINE IMINES; FORMAL TOTAL-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; SUBSTITUTED TETRAHYDROISOQUINOLINES; DIASTEREOSELECTIVE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; ISOQUINOLINE ALKALOIDS; HIGHLY EFFICIENT; TERTIARY-AMINES; DUAL CATALYSIS;

D O I：

10.1016/j.tet.2021.132121

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective route towards the synthesis of C-1 substituted tetrahydroisoquinoline natural products is reported. Six different natural products are synthesized from a single aldehyde using prolinecatalyzed asymmetric alpha-hydrazination reaction as the key step. The highly enantioselective introduction of an amino group is exploited to synthesize (-)-calycotomine, (-)-salsolidine, (-)-carnegine, (+)-homolaudanosine, (+)-homoprotoberberine and (thorn)-crispine A. (C) 2021 Elsevier Ltd. All rights reserved.

引用

页数：8

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