☆ 4.6 Review

Transition Metal-Catalyzed Enantioselective Synthesis of Chiral Five- and Six-Membered Benzo O-heterocycles

CHEMICAL RECORD (2023)

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Summary: In this study, a copper-catalyzed asymmetric cascade cyclization/[1,2]-Stevens-type rearrangement was reported to efficiently assemble a variety of valuable chiral chromeno[3,4-c]pyrroles bearing a quaternary carbon stereocenter with generally moderate to good yields and excellent enantioselectivities (up to 99% ee). Notably, this protocol represents the first example of catalytic asymmetric [1,2]-Stevens-type rearrangement based on alkynes and the first asymmetric formal carbene insertion into the Si-O bond.

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Summary: Intramolecular C-H insertions with donor/donor dirhodium carbenes provide a concise and highly stereoselective method to set two contiguous stereocenters in a single step. The study demonstrates that donor/donor carbenes undergo uniquely stereoselective reactions that originate from a stepwise reaction mechanism, in contrast to the analogous concerted reactions of carbenes with one or more electron-withdrawing groups attached.

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Summary: Asymmetric hydrogenation (AH) and asymmetric transfer hydrogenation (ATH) play crucial roles in the preparation of chiral compounds, particularly demonstrating remarkable performance in the synthesis of flavonoids.

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Bing Xu et al.

Summary: Recent research has shown that Heck-type difunctionalization of unactivated alkenes involving C-H bond activation has emerged as a powerful strategy. However, the development of asymmetric version has been lagging behind. In this study, we demonstrate a new method for the robust Heck-type difunctionalization of a broad range of unactivated alkenes through the first palladium/Xu-Phos-catalyzed tandem Heck/remote C-H bond alkylation.

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ACS CATALYSIS (2022)

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Recent Advances on the Construction of Chiral Dihydrobenzofurans by Asymmetric [3+2] Cyclization Reactions of Phenols (Quinones) and Alkenes

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Summary: Dihydrobenzofuran structural units are widely present in bioactive natural products and have attracted significant attention from synthetic organic chemists and pharmaceutical chemists. The enantioselective formation of this structural unit, particularly its chiral stereocenters, has been a challenging problem in synthetic methodology. Recent progress in asymmetric [3+2] cyclization reactions using different types of chiral catalysts and auxiliaries is summarized in this review, with an emphasis on understanding the control of stereoselectivities. The application of these reactions in the total synthesis of dihydrobenzofurans is also briefly introduced. Furthermore, the future development trend of asymmetric [3+2] cyclization reactions is analyzed in order to stimulate the emergence of highly efficient and general catalytic systems.

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Summary: This article summarizes the notable attempts made by the Trost group in the 1990s to synthesize several natural products through the palladium-catalyzed asymmetric allylic alkylation (AAA) reaction. It specifically focuses on Prof. Trost's contributions to chroman chemistry and the challenging C2 asymmetry synthesis.

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Research Progress on Asymmetric Synthesis of Flavanones

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Xiaoming Wang et al.

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Kangning Cao et al.

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ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Enantioselective Construction of 2-Aryl-2,3-dihydrobenzofuran Scaffolds Using Cu/SPDO-Catalyzed [3+2] Cycloaddition

Ze-Ran Jing et al.

Summary: A new and efficient method for the preparation of 2-aryl-2,3-dihydrobenzofuran scaffolds with excellent enantioselectivities and high yields has been developed through the Cu/SPDO-catalyzed [3 + 2] cycloaddition between quinone ester and styrene derivatives. Moreover, the asymmetric synthesis of natural corsifurans A and B from commercially available starting materials has been accomplished in two or three steps using this reaction as a key transformation.

ORGANIC LETTERS (2021)

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Article Chemistry, Physical

Catalytic Asymmetric C(sp3)-H Carbene Insertion Approach to Access Enantioenriched 3-Fluoroalkyl 2,3-Dihydrobenzofurans

Xinyu Zhang et al.

Summary: This study reports a novel enantioselective synthesis method, which enables the efficient synthesis of chiral fluoroalkyl derivatives by using fluoroalkyl N-triftosylhydrazones as the carbene source under mild conditions.

ACS CATALYSIS (2021)

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Review Chemistry, Multidisciplinary

Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications

Oscar Pamies et al.

Summary: This review covers the evolution, mechanistic understanding, and recent advances in enantioselective Pd-catalyzed allylic substitution, decarboxylative, and oxidative allylic substitutions. The catalytic data and examples of their application are collected, along with discussions on key mechanistic aspects for high selectivity and comparison with other metals. Different nucleophiles employed and ligand types for improved results in asymmetric allylic substitutions are highlighted.

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Bis(μ-oxo)-Dititanium(IV)-Chiral Binaphthyldisulfonate Complexes for Highly Enantioselective Intramolecular Hydroalkoxylation of Nonactivated Alkenes

Wen-Bin Xie et al.

Summary: A series of chiral compounds were designed and synthesized for a highly enantioselective intramolecular hydroalkoxylation of nonactivated alkenes, resulting in the formation of 2-methylcoumarans with up to 99% yields and up to 97% enantiomeric excess under mild conditions.

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Summary: A highly enantioselective palladium-catalyzed intermolecular tandem Heck/Cacchi reaction was developed for the synthesis of a broad range of enantioenriched compounds bearing all-carbon quaternary stereocenters of interest in pharmaceutical research. This method features inherent atom- and step-economy, high functional group tolerance, mild conditions, broad structural diversity, and excellent enantioselectivities.

CHINESE JOURNAL OF CHEMISTRY (2021)

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Yu Nie et al.

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ORGANIC LETTERS (2021)

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Lantao Liu et al.

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Transition metal-catalyzed addition reactions of arylboronic acids with alkyl 2-formylbenzoates: efficient access to chiral 3-substituted phthalides

Chun-Hui Xing et al.

CHEMICAL COMMUNICATIONS (2010)

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Article Chemistry, Multidisciplinary

Gold(I)-Catalyzed Enantioselective Polycyclization Reactions

Steven G. Sethofer et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

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Article Chemistry, Multidisciplinary

Enantioselective Copper-Catalyzed Intramolecular O-H Insertion: An Efficient Approach to Chiral 2-Carboxy Cyclic Ethers

Shou-Fei Zhu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

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Article Chemistry, Multidisciplinary

A C2-Symmetric Chiral Bis-Sulfoxide Ligand in a Rhodium-Catalyzed Reaction: Asymmetric 1,4-Addition of Sodium Tetraarylborates to Chromenones

Jun Chen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

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Article Chemistry, Inorganic & Nuclear

Enantioselective 6-endo-trig Wacker-type cyclization of 2-geranylphenols: application to a facile synthesis of (-)-cordiachromene

Kazuhiro Takenaka et al.

TETRAHEDRON-ASYMMETRY (2010)

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Article Chemistry, Multidisciplinary

Me-bipam for Enantioselective Ruthenium (II)-Catalyzed Arylation of Aldehydes with Arylboronic Acids

Yasunori Yamamoto et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

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Article Chemistry, Multidisciplinary

Synthesis of Chiral Tetrasubstituted Alkenes by an Asymmetric Cascade Reaction Catalyzed Cooperatively by Cationic Rhodium(I) and Silver(I) Complexes

Daiki Hojo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

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Article Chemistry, Multidisciplinary

Spiro[4,4]-1,6-nonadiene-Based Phosphine-Oxazoline Ligands for Iridium-Catalyzed Enantioselective Hydrogenation of Ketimines

Zhaobin Han et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

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Article Chemistry, Multidisciplinary

Asymmetric Dehydrative Cyclization of omega-Hydroxy Allyl Alcohols Catalyzed by Ruthenium Complexes

Shinji Tanaka et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

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Article Chemistry, Organic

Asymmetric Synthesis of Neolignans (-)-epi-Conocarpan and (+)-Conocarpan via Rh(II)-Catalyzed C-H Insertion Process and Revision of the Absolute Configuration of (-)-epi-Conocarpan

Yoshihiro Natori et al.

JOURNAL OF ORGANIC CHEMISTRY (2009)

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Article Chemistry, Multidisciplinary

Phthalides by Rhodium-Catalyzed Ketone Hydroacylation

Diem H. T. Phan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

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Article Chemistry, Organic

Catalytic Enantioselective Synthesis of Chiral Phthalides by Efficient Reductive Cyclization of 2-Acylarylcarboxylates under Aqueous Transfer Hydrogenation Conditions

Bo Zhang et al.

ORGANIC LETTERS (2009)

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Review Chemistry, Organic

Recent Progress in the Synthesis of 2,3-Dihydrobenzofurans

Ferruccio Bertolini et al.

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL (2009)

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Article Chemistry, Multidisciplinary

Enantioselective synthesis of spirocyclic benzopyranones by rhodium-catalyzed intermolecular [4+2] annulation

Daiki Hojo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

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Article Chemistry, Multidisciplinary

Asymmetric Intramolecular Oxa-Michael Addition of Activated alpha,beta-Unsaturated Ketones Catalyzed by a Chiral N,N '-Dioxide Nickel(II) Complex: Highly Enantioselective Synthesis of Flavanones

Lijia Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

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Review Chemistry, Multidisciplinary

Metal-catalyzed enantioselective allylation in asymmetric synthesis

Zhan Lu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

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Article Chemistry, Multidisciplinary

Stereoselective Synthesis of 4-Dehydroxydiversonol Employing Enantioselective Palladium-Catalysed Domino Reactions

Lutz F. Tietze et al.

CHEMISTRY-A EUROPEAN JOURNAL (2008)

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Article Chemistry, Medicinal

Advances toward New Antidepressants with Dual Serotonin Transporter and 5-HT1A Receptor Affinity within a Class of 3-Aminochroman Derivatives. Part 2

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JOURNAL OF MEDICINAL CHEMISTRY (2008)

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Article Chemistry, Medicinal

Novel 3-carboxamide-coumarins as potent and selective FXIIa inhibitors

Severine Robert et al.

JOURNAL OF MEDICINAL CHEMISTRY (2008)

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Article Chemistry, Organic

Enantioselective Synthesis of Chromanes by Iridium-Catalyzed Asymmetric Hydrogenation of 4H-Chromenes

Carine Valla et al.

SYNLETT (2008)

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Article Chemistry, Organic

Chelation-induced axially chiral palladium complex system with tetraoxazoline ligands for highly enantioselective Wacker-type cyclization

Yong Jian Zhang et al.

JOURNAL OF ORGANIC CHEMISTRY (2007)

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Article Chemistry, Multidisciplinary

Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes

Wei Zeng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

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Article Chemistry, Organic

Unusual heterochiral crystallization tendency of 3-arylphthalide compounds in non-racemic solution:: reinvestigation on asymmetric Ni-catalyzed tandem reaction of substituted o-halobenzaldehydes

Wen-Wen Chen et al.

TETRAHEDRON LETTERS (2007)

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Article Chemistry, Organic

Enantioselective synthesis of cis-α-substituted cycloalkanols and trans-cycloalkyl amines thereof

Rosario Fernandez et al.

TETRAHEDRON (2007)

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Article Oncology

Identification of griseofulvin as an inhibitor of centrosomal clustering in a phenotype-based screen

Blanka Rebacz et al.

CANCER RESEARCH (2007)

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Article Chemistry, Organic

Fumimycin:: A peptide deformylase inhibitor with an unusual skeleton produced by Aspergillus fumisynnematus

Yun-Ju Kwon et al.

ORGANIC LETTERS (2007)

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Article Chemistry, Organic

Highly enantioselective Pd(II)-catalyzed Wacker-type cyclization of 2-allylphenols by use of bisoxazoline ligands with axis-unfixed biphenyl backbone

Feijun Wang et al.

TETRAHEDRON LETTERS (2007)

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Article Chemistry, Organic

Atropisomeric bisoxazoline ligands with a bridge across the 5,5′-position of biphenyl for asymmetric catalysis

Feijun Wang et al.

TETRAHEDRON LETTERS (2007)

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Article Chemistry, Organic

Rhodium-catalyzed asymmetric one-pot transesterification and [2+2+2] cycloaddition leading to enantioenriched 3,3-disubstituted phthalides

Ken Tanaka et al.

ORGANIC LETTERS (2007)

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Review Chemistry, Multidisciplinary

Heterocycle synthesis by copper facilitated addition of heteroatoms to alkenes, alkynes and arenes

Sherry R. Chemler et al.

CHEMICAL SOCIETY REVIEWS (2007)

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Article Chemistry, Multidisciplinary

Highly efficient cyclization of o-iodobenzoates with aldehydes catalyzed by cobalt bidentate phosphine complexes:: A novel entry to chiral phthalides

Hong-Tai Chang et al.

CHEMISTRY-A EUROPEAN JOURNAL (2007)

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Article Chemistry, Multidisciplinary

Enantioselective palladium-catalyzed total synthesis of vitamin E by employing a domino Wacker-Heck reaction

Lutz F. Tietze et al.

CHEMISTRY-A EUROPEAN JOURNAL (2006)

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Review Chemistry, Multidisciplinary

C2-symmetric chiral bis(oxazoline) ligands in asymmetric catalysis

Giovanni Desimoni et al.

CHEMICAL REVIEWS (2006)

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Article Chemistry, Organic

Dirhodium tetracarboxylate derived from adamantylglycine as a chiral catalyst for carbenoid reactions

Ravisekhara P. Reddy et al.

ORGANIC LETTERS (2006)

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Review Chemistry, Organic

Palladium-catalyzed intramolecular asymmetric hydroamination, hydroalkoxylation, and hydrocarbonation of alkynes

Nitin T. Patil et al.

JOURNAL OF ORGANIC CHEMISTRY (2006)

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Article Chemistry, Multidisciplinary

Iridium catalysts with bicyclic pyridine-phosphinite ligands: Asymmetric hydrogenation of olefins and furan derivatives

Stefan Kaiser et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2006)

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Review Chemistry, Multidisciplinary

Oxidative cyclizations in a nonpolar solvent using molecular oxygen and studies on the stereochemistry of oxypalladation

RM Trend et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

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Article Chemistry, Multidisciplinary

Palladium-catalyzed enantioselective domino reaction for the efficient synthesis of vitamin E

LF Tietze et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)

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Article Chemistry, Multidisciplinary

Deuterium-labeling studies establishing stereochemistry at the oxypalladation step in Wacker-type oxidative cyclization of an o-allylphenol

T Hayashi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

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Article Chemistry, Multidisciplinary

Synthesis of chiral chromans by the Pd-catalyzed asymmetric allylic alkylation (AAA): Scope, mechanism, and applications

BM Trost et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

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Article Chemistry, Organic

Palladium-catalyzed asymmetric tandem allylic substitution using chiral 2-(phosphinophenyl)pyridine ligand

K Ito et al.

TETRAHEDRON LETTERS (2004)

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Article Chemistry, Physical

Palladium-catalyzed asymmetric hydrogenation of furan carboxylic acids

M Maris et al.

JOURNAL OF CATALYSIS (2003)

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Article Chemistry, Multidisciplinary

Unusual effects in the Pd-catalyzed asymmetric allylic alkylations: Synthesis of chiral chromans

BM Trost et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2003)

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Article Chemistry, Organic

Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereloselective synthesis of cis-disubstituted oxygen and nitrogen heterocycles

WH Cheung et al.

ORGANIC LETTERS (2003)

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Article Chemistry, Multidisciplinary

Palladium-catalyzed oxidative wacker cyclizations in nonpolar organic solvents with molecular oxygen: A stepping stone to asymmetric aerobic cyclizations

RM Trend et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2003)

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Article Chemistry, Organic

Enantio- and diastereoselective synthesis of cis-2-aryl-3-methoxycarbonyl-2,3-dihydrobenzofurans via the Rh(II)-catalyzed C-H insertion process

H Saito et al.

ORGANIC LETTERS (2002)

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Article Chemistry, Organic

Asymmetric intramolecular C-H insertions of aryldiazoacetates

HML Davies et al.

ORGANIC LETTERS (2001)

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Article Chemistry, Organic

Stereoselective synthesis of 3-substituted phtalides via asymmetric transfer hydrogenation using well-defined ruthenium catalysts under neutral conditions

K Everaere et al.

TETRAHEDRON LETTERS (2001)

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