Concise Access to Naphthalene Building Blocks for Naphthylisoquinoline Alkaloid Synthesis via Transition-Metal Catalysis

被引：0

作者：

Materis, Marios-Christoforos ^{[1
]}

van Otterlo, Willem A. L. ^{[2
]}

Berthold, Dino ^{[1
]}

机构：

[1] Ludwig Maximilians Univ Munchen, Dept Chem, Butenandtstr 5-13 Haus F, D-81377 Munich, Germany

[2] Stellenbosch Univ, Dept Chem & Polymer Sci, Private Bag 11, ZA-7602 Stellenbosch, Western Cape, South Africa

来源：

CHEMCATCHEM | 2024年 / 16卷 / 23期

关键词：

Naphthyl isoquinoline alkaloids; C-H oxidation; Hartwig's borylation; Transition-metal catalysis; Naphthalene functionalization; ACETOGENIC ISOQUINOLINE ALKALOIDS; MICHELLAMINES A-C; ANTIAUSTERITY ACTIVITIES; CONVENIENT SYNTHESIS; BORYLATION; LIANA; COMPLEXES; ARENES; KORUPENSAMINES; ANALOGS;

D O I：

10.1002/cctc.202401070

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A refined and therefore more (cost)efficient synthetic pathway towards 3-functionalized and orthogonally diprotected 5-bromo-1,8-dioxynaphthalenes is reported. The latter has been very recently employed as highly suitable building blocks for the total synthesis of 5-(naphtha-8-yl)isoquinoline alkaloids. Relying on the application of different transition-metal catalyzed reactions, namely C-H oxidation, Hartwig borylation and C,C cross-coupling reactions the desired precursors for future atroposelective synthesis of 5,8'-naphthylisoquinoline alkaloids and derivatives became accessible in a concise fashion.

引用

页数：7

共 69 条

[1]

[Anonymous], 2024, OUR SURVEY LOWEST PR

[2] Microwave-Assisted Solid-Liquid Phase Alkylation of Naphthols [J].

Balint, Erika ;

Kovacs, Orsolya ;

Drahos, Laszlo ;

Keglevich, Gyoergy .

LETTERS IN ORGANIC CHEMISTRY, 2013, 10 (05) :330-336

[3] Unprecedented Direct Asymmetric Total Syntheses of 5,8'-Naphthylisoquinoline Alkaloids from their Fully Substituted Precursors Employing a Novel Nickel/N,N-ligand-Catalyzed Atroposelective Cross-Coupling Reaction [J].

Berthold, Dino ;

van Otterlo, Willem .

CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (61)

[4] Ancisheynine, the first N,C-coupled naphthylisoquinoline alkaloid:: Total synthesis and stereochemical analysis [J].

Bringmann, G ;

Guider, T ;

Reichert, M ;

Meyer, F .

ORGANIC LETTERS, 2006, 8 (06) :1037-1040

[5] ACETOGENIC ISOQUINOLINE ALKALOIDS .66. FIRST TOTAL SYNTHESIS OF KORUPENSAMINE-A AND KORUPENSAMINE-B [J].

BRINGMANN, G ;

GOTZ, R ;

KELLER, PA ;

WALTER, R ;

HENSCHEL, P ;

SCHAFFER, M ;

STABLEIN, M ;

KELLY, TR ;

BOYD, MR .

HETEROCYCLES, 1994, 39 (02) :503-508

[6]

Bringmann G, 1996, LIEBIGS ANN, P2045

[7] Atroposelective biaryl coupling with chiral catalysts: Total synthesis of the antileishmanial naphthylisoquinoline alkaloids ancistrotanzanine B and ancistroealaine A [J].

Bringmann, G ;

Hamm, A ;

Schraut, M .

ORGANIC LETTERS, 2003, 5 (16) :2805-2808

[8]

Bringmann G., 1995, ALKALOIDS CHEM PHARM, P46

[9] Total synthesis of the antimalarial naphthylisoquinoline alkaloid 5-epi-4′-O-demethylancistrobertsonine C by asymmetric Suzuki cross-coupling [J].

Bringmann, Gerhard ;

Ruedenauer, Stefan ;

Bruhn, Torsten ;

Benson, Lauren ;

Brun, Reto .

TETRAHEDRON, 2008, 64 (23) :5563-5568

[10] Six naphthylisoquinoline alkaloids and a related benzopyranone from a Congolese Ancistrocladus species related to Ancistrocladus congolensis [J].

Bringmann, Gerhard ;

Spuziak, Joanna ;

Faber, Johan H. ;

Gulder, Tanja ;

Kajahn, Inga ;

Dreyer, Michael ;

Heubl, Guenther ;

Brun, Reto ;

Mudogo, Virima .

PHYTOCHEMISTRY, 2008, 69 (04) :1065-1075

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