Matsuda-Heck Arylation of Glycals for the Stereoselective Synthesis of Aryl C-Glycosides

被引：19

作者：

Otte, Fabian ^{[1
]}

Schmidt, Bernd ^{[1
]}

机构：

[1] Univ Potsdam, Inst Chem, Karl Liebknecht Str 24-25, D-14476 Potsdam, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 22期

关键词：

CROSS-COUPLING REACTIONS; ANION CAPTURE PROCESSES; HYDRIDE ION CAPTURE; DIAZONIUM SALTS; ARENEDIAZONIUM SALTS; STEREOCONTROLLED SYNTHESIS; NATURAL-PRODUCTS; PALLADIUM; PD/C; STRATEGIES;

D O I：

10.1021/acs.joc.9b02410

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The methoxymethyl-protected glycal L-amicetal, synthesized de novo from L-ethyl lactate through tandem ring-closing metathesis-isomerization sequence, undergoes a highly trans-diastereoselective Heck-type coupling reaction with various arene diazonium salts to furnish 2,3-unsaturated aryl C-glycosides in moderate to excellent yields. The products can be further functionalized, e.g., by hydrogenation, epoxidation, or dihydroxylation to furnish 2,3,6-tridesoxy, 2,3-anhydro-6-desoxy, or 6-desoxy aryl C-glycosides, respectively. The method was applied to the synthesis of an a-configured 6-desoxy-gliflozin derivative.

引用

页码：14816 / 14829

页数：14

共 94 条

[1] Synthetic Strategies toward SGLT2 Inhibitors [J].

Aguillon, Anderson R. ;

Mascarello, Alessandra ;

Segretti, Natanael D. ;

de Azevedo, Hatylas F. Z. ;

Guimaraes, Cristiano R. W. ;

Miranda, Leandro S. M. ;

de Souza, Rodrigo O. M. A. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2018, 22 (04) :467-488

[2] Enantioselective Heck-Matsuda Arylations through Chiral Anion Phase-Transfer of Aryl Diazonium Salts [J].

Avila, Carolina M. ;

Patel, Jigar S. ;

Reddi, Yernaidu ;

Saito, Masato ;

Nelson, Hosea M. ;

Shunatona, Hunter P. ;

Sigman, Matthew S. ;

Sunoj, Raghavan B. ;

Toste, F. Dean .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (21) :5806-5811

[3] Oxidative Heck Reaction of Glycals and Aryl Hydrazines: A Palladium-Catalyzed C-Glycosylation [J].

Bai, Yaguang ;

Kim, Le Mai Hoang ;

Liao, Hongze ;

Liu, Xue-Wei .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (17) :8821-8825

[4] 3-(2-Carboxyethyl)indole-2-carboxylic Acid Derivatives: Structural Requirements and Properties of Potent Agonists of the Orphan G Protein-Coupled Receptor GPR17 [J].

Baqi, Younis ;

Pillaiyar, Thanigaimalai ;

Abdelrahman, Aliaa ;

Kaufmann, Olesja ;

Aishaibani, Samer ;

Rafehi, Muhammad ;

Ghasimi, Saman ;

Akkari, Rhalid ;

Ritter, Kirsten ;

Simon, Katharina ;

Spinrath, Andreas ;

Kostenis, Evi ;

Zhao, Qiang ;

Koese, Meryem ;

Namasivayam, Vigneshwaran ;

Mueller, Christa E. .

JOURNAL OF MEDICINAL CHEMISTRY, 2018, 61 (18) :8136-8154

[5] Methods for 2-Deoxyglycoside Synthesis [J].

Bennett, Clay S. ;

Galan, M. Carmen .

CHEMICAL REVIEWS, 2018, 118 (17) :7931-7985

[6] Structure, activity, synthesis and biosynthesis of aryl-C-glycosides [J].

Bililign, T ;

Griffith, BR ;

Thorson, JS .

NATURAL PRODUCT REPORTS, 2005, 22 (06) :742-760

[7] Natural Products as Lead Compounds for Sodium Glucose Cotransporter (SGLT) Inhibitors [J].

Blaschek, Wolfgang .

PLANTA MEDICA, 2017, 83 (12-13) :985-993

[8] C-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential [J].

Bokor, Eva ;

Kun, Sandor ;

Goyard, David ;

Toth, Marietta ;

Praly, Jean-Pierre ;

Vidal, Sebastien ;

Somsak, Laszlo .

CHEMICAL REVIEWS, 2017, 117 (03) :1687-1764

[9] Base free aryl coupling of diazonium compounds and boronic esters: self-activation allowing an overall highly practical process [J].

Bonin, Helene ;

Delbrayelle, Dominique ;

Demonchaux, Patrice ;

Gras, Emmanuel .

CHEMICAL COMMUNICATIONS, 2010, 46 (15) :2677-2679

[10] PALLADIUM CATALYZED TANDEM CYCLIZATION ANION CAPTURE PROCESSES - HYDRIDE ION CAPTURE BY ALKYL-PALLADIUM AND PI-ALLYL-PALLADIUM SPECIES [J].

BURNS, B ;

GRIGG, R ;

RATANANUKUL, P ;

SRIDHARAN, V ;

STEVENSON, P ;

WORAKUN, T .

TETRAHEDRON LETTERS, 1988, 29 (34) :4329-4332

← 1 2 3 4 5 6 7 8 9 10 →