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

共 79 条

[1]

anchez-Obreg R. S, 2013, TETRAHEDRON LETT, V54, P1893

[2] Enantioselective Synthesis of (R)-Antofine and (R)-Cryptopleurine [J].

Ansari, Anas ;

Ramapanicker, Ramesh .

CHEMISTRYSELECT, 2018, 3 (44) :12591-12594

[3] Enantioselective Synthesis of 2-Aminomethyl and 3-Amino Pyrrolidines and Piperidines through 1,2-Diamination of Aldehydes [J].

Ansari, Anas ;

Ramapanicker, Ramesh .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (15) :8161-8169

[4] Transition states of amine-catalyzed aldol reactions involving enamine intermediates: Theoretical studies of mechanism, reactivity, and stereoselectivity [J].

Bahmanyar, S ;

Houk, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) :11273-11283

[5] Synthesis of Tetrahydroisoquinoline Alkaloids and Related Compounds through the Alkylation of Anodically Prepared α-Amino Nitriles [J].

Benmekhbi, Lotfi ;

Louafi, Fadila ;

Roisnel, Thierry ;

Hurvois, Jean-Pierre .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (15) :6721-6739

[6] β-Phenylethylamines and the isoquinoline alkaloids [J].

Bentley, KW .

NATURAL PRODUCT REPORTS, 2001, 18 (02) :148-170

[7]

Bergonzini G, 2014, CHEM SCI, V5, P112, DOI [10.1039/C3SC52265B, 10.1039/c3sc52265b]

[8] Enantioselective Synthesis of Tetrahydroprotoberberines and Bisbenzylisoquinoline Alkaloids from a Deprotonated α-Aminonitrile [J].

Blank, Nancy ;

Opatz, Till .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (23) :9777-9784

[9] A Comparative Mechanistic Study of Cu-Catalyzed Oxidative Coupling Reactions with N-Phenyltetrahydroisoquinoline [J].

Boess, Esther ;

Schmitz, Corinna ;

Klussmann, Martin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (11) :5317-5325

[10] Mechanistic Studies on a Cu-Catalyzed Aerobic Oxidative Coupling Reaction with N-Phenyl Tetrahydroisoquinoline: Structure of Intermediates and the Role of Methanol As a Solvent [J].

Boess, Esther ;

Sureshkumar, Devarajulu ;

Sud, Abhishek ;

Wirtz, Cornelia ;

Fares, Christophe ;

Klussmann, Martin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (21) :8106-8109

← 1 2 3 4 5 6 7 8 →