☆ 4.8 Article

An Oxidation and Ring Contraction Approach to the Synthesis of (+/-)-1-Deoxynojirimycin and (+/-)-1-Deoxyaltronojirimycin

ORGANIC LETTERS (2010)

Journal

ORGANIC LETTERS

Volume 12, Issue 1, Pages 136-139

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/ol902533b

Keywords

-

Categories

Chemistry, Organic

Ask authors/readers for more resources

Protocol

Community support

Reagent

Community support

Abstract

A reaction sequence involving the chemoselective olefinic oxidation of N(1)-benzyl-2,7-dihydro-1H-azepine with m-CPBA in the presence of HBF4 and BnOH followed by ring contraction facilitates the stereoselective preparation of either of the epoxide diastereoisomers of (2RS,3SR)-N(1)-benzyl-2-chloromethyl-3-benzyloxy-4,5-epoxypiperidine by simple modification of the reaction conditions. Epoxide ring opening, functional group interconversion, and deprotection allow the synthesis of (+/-)-1-deoxynojirimycin and (+/-)-1-deoxyaltronojirimycin.

Authors

I am an author on this paper

Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.8

Not enough ratings

Secondary Ratings

Novelty

-

Significance

-

Scientific rigor

-

Rate this paper

Recommended

Article Chemistry, Inorganic & Nuclear

Synthesis of Mo(IV) para-Substituted Styrene Complexes and an Exploration of Their Conversion to 1-Phenethylidene Complexes

Sumeng Liu, Matthew P. Conley, Richard R. Schrock

Summary: Molybdenum(IV) styrene complexes were synthesized and their conversion was investigated. It was found that the two isomers of styrene can interconvert through protonation, and the rate-limiting step is the protonation of styrene. The rate of protonation was found to be dependent on the substituent.

ORGANOMETALLICS (2022)

Add to Collection

Article Computer Science, Interdisciplinary Applications

An efficient and scalable approach to hub location problems based on contraction

Sebastian Wandelt, Weibin Dai, Jun Zhang, Qiuhong Zhao, Xiaoqian Sun

Summary: This paper introduces a new hub location method, EHLC, which efficiently computes hub locations on a simplified network instance and optimizes the final solution on the original network, outperforming existing solution techniques by orders of magnitude in terms of execution time and achieving solutions with identical gaps for almost all datasets and parameter combinations.

COMPUTERS & INDUSTRIAL ENGINEERING (2021)

Add to Collection

Article Chemistry, Organic

Hymoins A-D: Two Pairs of Polyprenylated Acylphloroglucinols from Hypericum monogynum and Their Light-Induced Transformation

Yan-Rong Zeng, Chun-Mao Yuan, Ya-Nan Li, Lie-Jun Huang, Zhan-Xing Hu, Wei Gu, Xiao-Jiang Hao

Summary: Two pairs of light-induced transformative polyprenylated acylphloroglucinols with an unprecedented pentacyclic skeleton were isolated from the flowers of Hypericum monogynum. The first decarbonylative ring contraction of complex natural products was investigated by light irradiation. Their structures were elucidated by nuclear magnetic resonance analysis, X-ray crystallography, and electronic circular dichroism calculations, with compound 3 showing moderate inhibition efficacy of the platelet-activating-factor-induced aggregation of rabbit platelets.

ORGANIC LETTERS (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Diastereodivergent Synthesis of Cyclopentyl Boronic Esters Bearing Contiguous Fully Substituted Stereocenters

Molly E. Fairchild, Adam Noble, Varinder K. Aggarwal

Summary: This study reported the synthesis of cyclopentyl boronic esters bearing two contiguous, fully substituted stereocenters via electrophile-induced ring contractive 1,2-metallate rearrangement, with diastereodivergent construction achieved by simple variation of the reaction solvent. The utility of this methodology was demonstrated in the asymmetric total synthesis of (+)-herbertene-1,14-diol.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Biosynthesis of AS2077715 and Funiculosin: Pathway Reconstitution and Identification of Enzymes that Form the All-cis Cyclopentanetetraol Moiety

Bruno Perlatti, Gerald F. Bills, Masao Ohashi, Yi Tang, Yalong Zhang, Eun Bin Go

Summary: The biosynthesis of the antifungals AS2077715 and funiculosin involves a five-enzyme cascade that allows the conversion of a hydroxyphenyl-containing precursor into an unusual all-cis cyclopentanetetraol moiety. The cascade includes a multifunctional flavin-dependent monooxygenase and a repurposed O-methyltransferase.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

Add to Collection

Article Chemistry, Multidisciplinary

A Photochemical Strategy for ortho-Aminophenol Synthesis via Dearomative-Rearomative Coupling Between Aryl Azides and Alcohols

Bo Li, Alessandro Ruffoni, Daniele Leonori

Summary: ortho-Aminophenols are commonly found in many high-value materials and are generally prepared using electrophilic aromatic substitution chemistry. However, this method is not suitable for substrates with a specific arrangement of N- and O-groups. In this study, an alternative strategy using aryl azides as precursors was reported, which utilized low-energy photoexcitation to trigger the decomposition of aryl azides and allowed the introduction of alcoholic nucleophiles into aromatic compounds.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Add to Collection

Article Chemistry, Multidisciplinary

Simultaneous Ring Contraction and Expansion Reaction: Electrosynthesis of Heterocycle-Fused Fulleroids and Photovoltaic Application

Zheng-Chun Yin, Mingjie Li, Chuang Niu, Wei-Feng Wang, Wen-Rui Liu, Qian-Wen Zhang, Guan-Wu Wang

Summary: This study achieves the reductive electrosynthesis of heterocycle-fused fulleroids from fullerotetrahydropyridazines and electrophiles in the presence of a trace amount of oxygen, with concurrent ring contraction and expansion reactions. Depending on the electrophiles used, different regioselective formations of heterocycle-fused fulleroids are achieved. The reaction proceeds through multiple steps, and the structures of the synthesized fulleroids have been determined and their high regioselectivities rationalized by theoretical calculations.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Add to Collection

Article Chemistry, Applied

Switchable Bronsted Acid-Catalyzed Ring Contraction of Cyclooctatetraene Oxide Towards the Enantioselective Synthesis of Cycloheptatrienyl-Substituted Homoallylic Alcohols and Oxaborinanes

Jana Sendra, Oriol Salvado, Manuel Pedron, Efraim Reyes, Tomas Tejero, Elena Fernandez, Pedro Merino, Jose L. Vicario

Summary: The ability of cyclooctatetraene oxide to undergo ring contraction events under mild conditions using Bronsted acid catalysis has been investigated. Selectivity was found to be controlled by catalyst acidity and temperature, leading to either cycloheptatriene carbaldehyde or phenylacetaldehyde products. A mechanistic understanding of the reaction and the influence of the catalyst has been provided through experimental and computational data. Moreover, the acid-catalyzed ring contraction has been combined with in situ enantioselective allylation reaction, resulting in enantioenriched cycloheptatrienyl-substituted homoallylic alcohols. These alcohols have further been converted to enantioenriched oxaborinanes through copper-catalyzed nucleophilic borylation/cyclization protocol.

ADVANCED SYNTHESIS & CATALYSIS (2023)

Add to Collection

Article Chemistry, Organic

From Ring-Expansion to Ring-Contraction: Synthesis of γ-Lactones from Cyclobutanols and Relative Stability of Five- and Six-Membered Endoperoxides toward Organic Bases

Nicolas Jamey, Laurent Ferrie

Summary: This study reports the ring expansion reaction of cyclobutanols with molecular oxygen and the generalization of ring contraction through a rearrangement reaction. It also reveals the difference in stability between 1,2-dioxane and 1,2-dioxolane against organic bases.

SYNTHESIS-STUTTGART (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Dinitrogen extrusion from diazene in organic synthesis

Chunngai Hui, Shiping Wang, Chunfa Xu

Summary: This article reviews the methods and applications of using diazenes to construct complex molecular scaffolds through radical-mediated reactions. By undergoing nitrogen extrusion under thermal or photochemical conditions, biradical species with superior reactivity and chemoselectivity can be generated, which have been applied in the synthesis of natural products.

CHINESE CHEMICAL LETTERS (2022)

Add to Collection

Article Chemistry, Organic

Synthesis of noradamantane derivatives by ring-contraction of the adamantane framework

Benjamin Zonker, Jonathan Becker, Radim Hrdina

Summary: The study describes a triflic acid promoted cascade reaction involving decarboxylation of N-methyl protected cyclic carbamates and subsequent intramolecular nucleophilic 1,2-alkyl shift to generate ring contracted iminium triflates. This reaction allows for the preparation of noradamantane derivatives in a few steps from simple hydroxy-substituted adamantane precursors, expanding the family of similar transformations.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Add to Collection

Article Chemistry, Organic

Synthesis and Biological Evaluation of Highly Potent Fungicidal Deoxy-Hygrophorones

Toni Ditfe, Eileen Bette, Haider N. Sultani, Alexander Otto, Ludger A. Wessjohann, Norbert Arnold, Bernhard Westermann

Summary: Racemic di- and mono-hydroxylated cyclopentenones with aliphatic side chains were synthesized from furfuryl aldehyde based on naturally occurring hygrophorones. Different synthetic pathways were employed for trans-configured di- and mono-hydroxylated derivatives, all of which showed good to excellent fungicidal activities against plant pathogens.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Organic

Synthesis of 2-(2-Pyridyl)-2H-azirines via Metal-Free C-C Cross-Coupling of Bromoazirines with 2-Stannylpyridines

Anastasiya Agafonova, Ilia A. Smetanin, Nikolai Rostovskii, Alexander F. Khlebnikov, Mikhail S. Novikov

Summary: This study presents a high-yield method for introducing a 2-pyridyl substituent in the C2 position of the three-membered ring of 2-bromo-2H-azirine-2-carboxylic acid derivatives through direct cross-coupling with 2-(trialkylstannyl)pyridines. The reaction is versatile, working well with different substituted 2-stannylpyridines and enabling the synthesis of 2-(thiazol-2-yl)-2H-azirines. DFT calculations suggest that the reaction proceeds through a sequence of S(N)2'-substitution, 1,4-stannyl shift, and [2,3]-sigmatropic shift of the pyridine ring.

ORGANIC LETTERS (2021)

Add to Collection

Article Chemistry, Organic

A Sulfur-Controlled Approach to the Synthesis of Linerixibat

Gregg A. Barcan, Doo-Hyun Kwon, Jiasheng Guo, John A. Kowalski, Li Liu, Mark Nilson, Jack Sisko, Huan Wang, Timothy A. Brown, Habib Gholipour-Ranjbar

Summary: Establishing the two stereocenters in the benzothiaze-pine ring of linerixibat (GSK2330672) has always been a long-standing problem at GSK. Our solution is based on an episulfonium-controlled Ritter reaction followed by a sulfoxide-directed reduction. Both steps are supported by literature precedent and computational experiments. Transition state modeling suggests that the sulfoxide-directed reduction proceeds through electronic repulsion between the lone pair of electrons on sulfur and the incoming borohydride anion.

JOURNAL OF ORGANIC CHEMISTRY (2023)

Add to Collection

Article Chemistry, Multidisciplinary

Cyclisations and Strategies for Stereoselective Synthesis of Piperidine Iminosugars

Debashis Dhara, Ashis Dhara, Jack Bennett, Paul Murphy

Summary: This personal account focuses on the synthesis of polyhydroxylated piperidines, a subset of compounds within the iminosugar family, using various cyclisation methods and enantiomerically pure precursors to obtain substituted piperidines. The laboratory has contributed cascades based on reductive amination and Huisgen azide-alkene cycloaddition for the synthesis of substituted piperidines with quaternary centres adjacent to nitrogen.

CHEMICAL RECORD (2021)

Add to Collection

Article Oncology

Disrupting Hypoxia-Induced Bicarbonate Transport Acidifies Tumor Cells and Suppresses Tumor Growth

Alan McIntyre, Alzbeta Hulikova, Ioanna Ledaki, Cameron Snell, Dean Singleton, Graham Steers, Peter Seden, Dylan Jones, Esther Bridges, Simon Wigfield, Ji-Liang Li, Angela Russell, Pawel Swietach, Adrian L. Harris

CANCER RESEARCH (2016)

Add to Collection

Article Chemistry, Inorganic & Nuclear

Strategies for the construction of morphinan alkaloid AB-rings: regioselective Friedel-Crafts-type cyclisations of γ-aryl-β-benzoylamido acids with asymmetrically substituted γ-aryl rings

Stephen G. Davies, Euan C. Goddard, Paul M. Roberts, Angela J. Russell, Andrew D. Smith, James E. Thomson, Jonathan M. Withey

TETRAHEDRON-ASYMMETRY (2016)

Add to Collection

Article Chemistry, Organic

Probing Competitive and Co-operative Hydroxyl and Ammonium Hydrogen-Bonding Directed Epoxidations

Marta Brambilla, Meabh B. Brennan, Kristina Csatayova, Stephen G. Davies, Ai M. Fletcher, Alice M. R. Kennett, James A. Lee, Paul M. Roberts, Angela J. Russell, James E. Thomson

JOURNAL OF ORGANIC CHEMISTRY (2017)

Add to Collection

Article Pharmacology & Pharmacy

A Genomic DNA Reporter Screen Identifies Squalene Synthase Inhibitors That Act Cooperatively with Statins to Upregulate the Low-Density Lipoprotein Receptor

Alastair G. Kerr, Lawrence C. S. Tam, Ashley B. Hale, Milena Cioroch, Gillian Douglas, Sarina Agkatsev, Olivia Hibbitt, Joseph Mason, James Holt-Martyn, Carole J. R. Bataille, Graham M. Wynne, Keith M. Channon, Angela J. Russell, Richard Wade-Martins

JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS (2017)

Add to Collection

Article Infectious Diseases

Dihydrobenz[e][1,4] oxazepin-2(3H)-ones, a new anthelmintic chemotype immobilising whipworm and reducing infectivity in vivo

Frederick A. Partridge, Emma A. Murphy, Nicky J. Willis, Carole J. R. Bataille, Ruth Forman, Narinder Heyer-Chauhan, Bruno Marinic, Daniel J. C. Sowood, Graham M. Wynne, Kathryn J. Else, Angela J. Russell, David B. Sattelle

PLOS NEGLECTED TROPICAL DISEASES (2017)

Add to Collection

Review Biochemistry & Molecular Biology

The Role of Metabolite-Sensing G Protein-Coupled Receptors in Inflammation and Metabolic Disease

Carlota Recio, Daniel Lucy, Poppy Iveson, Asif J. Iqbal, Sophia Valaris, Graham Wynne, Angela J. Russell, Robin P. Choudhury, Chris O'Callaghan, Claudia Monaco, David R. Greaves

ANTIOXIDANTS & REDOX SIGNALING (2018)

Add to Collection

Article Pharmacology & Pharmacy

Simvastatin activates single skeletal RyR1 channels but exerts more complex regulation of the cardiac RyR2 isoform

Elisa Venturi, Chris Lindsay, Sabine Lotteau, Zhaokang Yang, Emma Steer, Katja Witschas, Abigail D. Wilson, James R. Wickens, Angela J. Russell, Derek Steele, Sarah Calaghan, Rebecca Sitsapesan

BRITISH JOURNAL OF PHARMACOLOGY (2018)

Add to Collection

Article Chemistry, Organic

The Dimroth rearrangement as a probable cause for structural misassignments in imidazo[1,2-a]pyrimidines: A N-15-labelling study and an easy method for the determination of regiochemistry

Maria Chatzopoulou, R. Fernando Martinez, Nicky J. Willis, Timothy D. W. Claridge, Francis X. Wilson, Graham M. Wynne, Stephen G. Davies, Angela J. Russell

TETRAHEDRON (2018)

Add to Collection

Article Infectious Diseases

2,4-Diaminothieno[3,2-d]pyrimidines, a new class of anthelmintic with activity against adult and egg stages of whipworm

Frederick A. Partridge, Ruth Forman, Nicky J. Willis, Carole J. R. Bataille, Emma A. Murphy, Anwen E. Brown, Narinder Heyer-Chauhan, Bruno Marinic, Daniel J. C. Sowood, Graham M. Wynne, Kathryn J. Else, Angela J. Russell, David B. Sattelle

PLOS NEGLECTED TROPICAL DISEASES (2018)

Add to Collection

Article Biology

BRET-based RAS biosensors that show a novel small molecule is an inhibitor of RAS-effector protein-protein interactions

Nicolas Bery, Abimael Cruz-Migoni, Carole J. R. Bataille, Camilo E. Quevedo, Hanna Tulmin, Ami Miller, Angela Russell, Simon E. V. Phillips, Stephen B. Carr, Terence H. Rabbitts

ELIFE (2018)

Add to Collection

Article Parasitology

An automated high-throughput system for phenotypic screening of chemical libraries on C. elegans and parasitic nematodes

Frederick A. Partridge, Anwen E. Brown, Steven D. Buckingham, Nicky J. Willis, Graham M. Wynne, Ruth Forman, Kathryn J. Else, Alison A. Morrison, Jacqueline B. Matthews, Angela J. Russell, David A. Lomas, David B. Sattelle

INTERNATIONAL JOURNAL FOR PARASITOLOGY-DRUGS AND DRUG RESISTANCE (2018)

Add to Collection

Article Immunology

Activation of the Immune-Metabolic Receptor GPR84 Enhances Inflammation and Phagocytosis in Macrophages

Carlota Recio, Daniel Lucy, Gareth S. D. Purvis, Poppy Iveson, Lynda Zeboudj, Asif J. Iqbal, Daniel Lin, Chris O'Callaghan, Lucy Davison, Esther Griesbach, Angela J. Russell, Graham M. Wynne, Lea Dib, Claudia Monaco, David R. Greaves

FRONTIERS IN IMMUNOLOGY (2018)

Add to Collection

Article Biochemistry & Molecular Biology

Chemical Instability and Promiscuity of Arylmethylidenepyrazolinone-Based MDMX Inhibitors

Jakub Stefaniak, Andrew M. Lewis, Daniel Conole, Sebastien R. G. Galan, Carole J. R. Bataille, Graham M. Wynne, M. Paola Castaldi, Thomas Lundback, Angela J. Russell, Kilian V. M. Huber

ACS CHEMICAL BIOLOGY (2018)

Add to Collection

Article Multidisciplinary Sciences

Small molecule inhibitors of RAS-effector protein interactions derived using an intracellular antibody fragment

Camilo E. Quevedo, Abimael Cruz-Migoni, Nicolas Bery, Ami Miller, Tomoyuki Tanaka, Donna Petch, Carole J. R. Bataille, Lydia Y. W. Lee, Phillip S. Fallon, Hanna Tulmin, Matthias T. Ehebauer, Narcis Fernandez-Fuentes, Angela J. Russell, Stephen B. Carr, Simon E. V. Phillips, Terence H. Rabbitts

NATURE COMMUNICATIONS (2018)

Add to Collection

Article Biochemistry & Molecular Biology

Thiazolidine derivatives as potent and selective inhibitors of the PIM kinase family

Carole J. R. Bataille, Meabh B. Brennan, Simon Byrne, Stephen G. Davies, Matthew Durbin, Oleg Fedorov, Kilian V. M. Huber, Alan M. Jones, Stefan Knapp, Gu Liu, Anna Nadali, Camilo E. Quevedo, Angela J. Russell, Roderick G. Walker, Robert Westwood, Graham M. Wynne

BIOORGANIC & MEDICINAL CHEMISTRY (2017)

Add to Collection

No Data Available

© Peeref 2019-2024. All rights reserved.