Advances in Organic Synthesis: Volume 13 E-Book

• Herausgeber: Bentham Science Publishers
• Kategorie: Wissenschaft und neue Technologien
• Serie: Advances in Organic Synthesis
• Sprache: Englisch

Seitenzahl: 358

Veröffentlichungsjahr: 2020

Beschreibung

Advances in Organic Synthesis is abook series devoted to the latest advances in synthetic approaches towardschallenging structures. The series presents comprehensive reviews written byeminent authorities on different synthetic approaches to selected targetmolecules and new methods developed to achieve specific synthetictransformations or optimal product yields. Advances in Organic Synthesisis essential for all organic chemists in academia and the industry who wish tokeep abreast of rapid and important developments in the field. This volume presents the following reviews:Electroluminescent polymers - a review on synthesis from organic compoundsRemarkable advances in the asymmetric synthesis of biologically active natural compounds from the advent of chiral auxiliariesThe chemistry of ynamides and their application in organic synthesisCarbon-heteroatom bond formation for medium ring heterocyclesTin(ii) salts: versatile and efficient lewis acid catalysts in reactions to add value to the glycerol and terpenic alcohols(E)-n-methyl-1-(methylthio)-2-nitroethenamine (nmsm) as a versatile ambiphilic synthon in organic synthesis

Leseprobe

Table of Contents

BENTHAM SCIENCE PUBLISHERS LTD.

End User License Agreement (for non-institutional, personal use)

Usage Rules:

Disclaimer:

Limitation of Liability:

General:

PREFACE

List of Contributors

Remarkable Advances in the Asymmetric Synthesis of Biologically Active Natural Compounds from the Advent of Chiral Auxiliaries

Abstract

INTRODUCTION

EVANS’ OXAZOLIDINONES

Asymmetric Aldol Reactions by Using Evans’ Oxazolidinones

Preparation of the Spiroketal Subunit (1)

Preparation of the Polyol Glycoside Subunit (2)

Synthesis of (−)-Cytovaricin

COREY’S CHIRAL AUXILIARY: (+)-8-PHENYLMENTHOL

ENDERS’ CHIRAL AUXILIARIES

CHIRAL AUXILIARIES OF YAMADA

OPPOLZER’S CHIRAL AUXILIARY

CARBOHYDRATES AS CHIRAL AUXILIARIES – KUNZ’S AUXILIARIES

Asymmetric Reaction of Strecker Employing Kunz's Galactosylamine

Asymmetric Mannich Reaction Employing the Galactosylamine of Kunz

MEYERS CHIRAL OXAZOLINES

AMINO ACIDS AS CHIRAL AUXILIARIES – SCHÖLLKOPF AUXILIARIES

CONCLUSIONS

LIST OF ABBREVIATIONS

CONSENT FOR PUBLICATION

CONFLICT OF INTEREST

ACKNOWLEDGEMENTS

REFERENCES

The Chemistry of Ynamide and Its Application in Organic Synthesis

Abstract

INTRODUCTION

PREPARATIONS OF YNAMIDES

Dehydrohalogenation

Alkynyliodonium Salts

Ullmann Coupling of Amides

Oxidative Coupling

Functionalization of Terminal Ynamides

Strained Cyclic Ynamide

REACTIONS OF YNAMIDES

Addition Reaction

Addition to α-Position of Ynamides

With Carbon-Halogen Bond Formation

With Carbon-Oxygen Bond Formation

With Carbon-Carbon Bond Formation

With Carbon-Nitrogen Bond Formation

Addition to β-Position of Ynamides

With Carbon-Boron Bond Formation

With Carbon-Carbon Bond Formation

With Carbon-Phosphorus Bond Formation

With Carbon-Nitrogen Bond Formation

With Carbon-Silicon Bond Formation

Radical Process

Oxidation

Rearrangement

Cyclization

Metal-Free or Lewis Acid Mediated Cyclization

Gold-Mediated Cyclization

Copper-Mediated Cyclization

Palladium-Mediated Cyclization

Rhodium-Mediated Cyclization

Cycloaddition

[2+1]

[2+2]

[3+2]

[4+1]

[4+2]

[2+2+2]

[5+2]

CONCLUSION

CONSENT FOR PUBLICATION

CONFLICT OF INTEREST

ACKNOWLEDGEMENTS

REFERENCES

Carbon-Heteroatom Bond Formation for Medium Ring Heterocycles

Abstract

INTRODUCTION

STRUCTURAL EFFECTS

RINGS WITH HETEROATOMS OTHER THAN O, N, AND S

SYNTHETIC METHODS

STRATEGIES FOR C-X BOND FORMATION

SYNTHESIS OF 7-MEMBERED RINGS

TRANSITION METAL CATALYZED REACTIONS

GREEN SYNTHESIS

NUCLEOPHILIC CYCLIZATION

REARRANGEMENT REACTIONS

SYNTHESIS OF 8-MEMBERED RINGS

TRANSITION METAL CATALYZED REACTIONS

NUCLEOPHILIC CYCLIZATION

REARRANGEMENT REACTIONS

SYNTHESIS OF 9-MEMBERED RINGS

Transition Metal Catalyzed Reactions

NUCLEOPHILIC CYCLIZATION

OXIDATIVE REARRANGEMENTS

CONCLUSION

CONFLICT OF INTEREST

ACKNOWLEDGEMENTS

LIST OF ABBREVIATIONS

REFERENCES

Tin(II) Salts: A Versatile and Efficient Lewis Acid Catalyst in Reactions to Add Value to the Glycerol and Terpenic Alcohols

Abstract

INTRODUCTION

Sncl2 Or Snf2-Catalyzed Solketal Synthesis

Sn(II)-Catalyzed Terpenic Alcohol Esterification With Acetic Acid

CONCLUDING REMARKS

CONSENT FOR PUBLICATION

CONFLICT OF INTEREST

ACKNOWLEDGEMENTS

REFERENCES

(E)-N-Methyl-1-(Methylthio)-2-Nitroethenamine (Nmsm) as a Versatile Ambiphilic Synthon in Organic Synthesis

Abstract

INTRODUCTION

Preparation of NMSM

APPLICATIONS OF NMSM IN THE SYNTHESIS OF HETEROCYCLES

Single Ring Heterocyclic Derivatives

Dihydropyridines

Pyridones

4h-Pyrans

Pyrimidinones

Pyrroles

Thiophenes

Isoxazoles

Fused heterocycle derivatives

4H-chromenes

4h-Chromenones

Pyranochromenones

Benzochromenes

Benzochromene-Diones

Pyranocarbazoles

Pyranopyrazoles

Pyranopyranones

Pyranoquinolinones

Pyrazolopyridines

Pyranopyrimidines

Imidazopyrimidines

Indenopyrroles

Bis-Heterocyclic Compounds

Indolylpyrans

Chromenopyrazoles

Pyrrolylpyrimidines

Spiroheterocycles

Spiroindolines

Spiro-4h-Pyrans

Bulk Drug Synthesis (Industrial Applications)

Ranitidine

Nizatidine

CONCLUSION

CONSENT FOR PUBLICATION

CONFLICT OF INTEREST

ACKNOWLEDGEMENTS

REFERENCES

Advances in Organic Synthesis

(Volume 13)

Edited by

Atta-ur-Rahman, FRS

Kings College,

University of Cambridge,

Cambridge,

UK

BENTHAM SCIENCE PUBLISHERS LTD.

End User License Agreement (for non-institutional, personal use)

This is an agreement between you and Bentham Science Publishers Ltd. Please read this License Agreement carefully before using the ebook/echapter/ejournal (“Work”). Your use of the Work constitutes your agreement to the terms and conditions set forth in this License Agreement. If you do not agree to these terms and conditions then you should not use the Work.

Bentham Science Publishers agrees to grant you a non-exclusive, non-transferable limited license to use the Work subject to and in accordance with the following terms and conditions. This License Agreement is for non-library, personal use only. For a library / institutional / multi user license in respect of the Work, please contact: [email protected].

Usage Rules:

All rights reserved: The Work is the subject of copyright and Bentham Science Publishers either owns the Work (and the copyright in it) or is licensed to distribute the Work. You shall not copy, reproduce, modify, remove, delete, augment, add to, publish, transmit, sell, resell, create derivative works from, or in any way exploit the Work or make the Work available for others to do any of the same, in any form or by any means, in whole or in part, in each case without the prior written permission of Bentham Science Publishers, unless stated otherwise in this License Agreement.You may download a copy of the Work on one occasion to one personal computer (including tablet, laptop, desktop, or other such devices). You may make one back-up copy of the Work to avoid losing it.The unauthorised use or distribution of copyrighted or other proprietary content is illegal and could subject you to liability for substantial money damages. You will be liable for any damage resulting from your misuse of the Work or any violation of this License Agreement, including any infringement by you of copyrights or proprietary rights.

Disclaimer:

Bentham Science Publishers does not guarantee that the information in the Work is error-free, or warrant that it will meet your requirements or that access to the Work will be uninterrupted or error-free. The Work is provided "as is" without warranty of any kind, either express or implied or statutory, including, without limitation, implied warranties of merchantability and fitness for a particular purpose. The entire risk as to the results and performance of the Work is assumed by you. No responsibility is assumed by Bentham Science Publishers, its staff, editors and/or authors for any injury and/or damage to persons or property as a matter of products liability, negligence or otherwise, or from any use or operation of any methods, products instruction, advertisements or ideas contained in the Work.

Limitation of Liability:

In no event will Bentham Science Publishers, its staff, editors and/or authors, be liable for any damages, including, without limitation, special, incidental and/or consequential damages and/or damages for lost data and/or profits arising out of (whether directly or indirectly) the use or inability to use the Work. The entire liability of Bentham Science Publishers shall be limited to the amount actually paid by you for the Work.

General:

Any dispute or claim arising out of or in connection with this License Agreement or the Work (including non-contractual disputes or claims) will be governed by and construed in accordance with the laws of Singapore. Each party agrees that the courts of the state of Singapore shall have exclusive jurisdiction to settle any dispute or claim arising out of or in connection with this License Agreement or the Work (including non-contractual disputes or claims).Your rights under this License Agreement will automatically terminate without notice and without the need for a court order if at any point you breach any terms of this License Agreement. In no event will any delay or failure by Bentham Science Publishers in enforcing your compliance with this License Agreement constitute a waiver of any of its rights.You acknowledge that you have read this License Agreement, and agree to be bound by its terms and conditions. To the extent that any other terms and conditions presented on any website of Bentham Science Publishers conflict with, or are inconsistent with, the terms and conditions set out in this License Agreement, you acknowledge that the terms and conditions set out in this License Agreement shall prevail.

Bentham Science Publishers Pte. Ltd. 80 Robinson Road #02-00 Singapore 068898 Singapore Email: [email protected]

PREFACE

This volume of Advances in Organic Synthesis presents recent exciting developments in synthetic organic chemistry. It covers a range of topics including important researches on novel approaches to the construction of complex organic compounds. The chapters are written by authorities in the field. Topics covered in this volume include updates in asymmetric synthesis of natural compounds, ynamide chemistry and its application in organic synthesis, heterocyclic chemistry, application of tin(II) salts in specific organic reactions and the use of (E)-N-methyl-1-(methylthio)-2-nitroethenamine (NMSM) as an ambiphilic synthon in organic synthesis.

This book should prove to be a valuable resource source for organic chemists, pharmaceutical scientists and postgraduate students seeking updated and critically important information on recent important developments in synthetic organic chemistry. I hope that the readers will find these reviews valuable and thought-provoking so that they may trigger further research in the quest for new developments in the field.

I am thankful to the efficient team of Bentham Science Publishers for the timely efforts made by the editorial personnel, especially Mr. Mahmood Alam (Director Publications), Mr. Obaid Sadiq (in-charge Books Department) and Ms. Asma Ahmed (Manager Publications).

Prof. Atta-ur-Rahman, FRS Kings College University of Cambridge Cambridge UK

List of Contributors

Bhaskar ChatterjeeNabadwip Vidyasagar College, Nadia, West Bengal, IndiaDhananjoy MondalSchool of Chemical Sciences, Central University of Gujarat, Gandhi-nagar, 382030 , IndiaDaniele Cristina de RezendeDepartment of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais 31270-901, BrazilFernanda Rodrigues NascimentoDepartment of Biochemistry and Molecular Biology, Universidade Federal de Viçosa, Viçosa, Minas Gerais, 36570-900, BrazilGaspar Diaz-MuñozDepartment of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais 31270-901, BrazilIzabel Luzia MirandaDepartment of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais 31270-901, BrazilJefferson Viktor Barros de Paula BaetaDepartment of Biochemistry and Molecular Biology, Universidade Federal de Viçosa, Viçosa, Minas Gerais, 36570-900, BrazilMarisa Alves Nogueira DiazDepartment of Biochemistry and Molecular Biology, Universidade Federal de Viçosa, Viçosa, Minas Gerais, 36570-900, BrazilMarcio J. da SilvaDepartment of Chemistry, Federal University of Vicosa, Vicosa, BrazilMilena G. TeixeiraDepartment of Chemistry, Federal University of Vicosa, Vicosa, BrazilNa WuState Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University , Guilin, 541004, P.R., China Chemistry Department, Science Site, Durham University, South Road, DH1-3LE, United KingdomPrateek BhambooSchool of Chemical Sciences, Central University of Gujarat, Gandhi-nagar, 382030 , IndiaPedavenkatagari Narayana ReddyDepartment of Chemistry, School of Science, Gitam University, Hyderabad, IndiaPannala PadmajaCentre for Semio Chemicals, CSIR-Indian Institute of Chemical Technology, Hyderabad, IndiaSuélen Karine SartoriDepartment of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais 31270-901, BrazilSmritilekha BeraSchool of Chemical Sciences, Central University of Gujarat, Gandhi-nagar, 382030, IndiaSiyu YeState Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University , Guilin, 541004, P.R., China

Remarkable Advances in the Asymmetric Synthesis of Biologically Active Natural Compounds from the Advent of Chiral Auxiliaries

Gaspar Diaz-Muñoz1,*,Izabel Luzia Miranda1,Suélen Karine Sartori1,Daniele Cristina de Rezende1,Jefferson Viktor Barros de Paula Baeta2,Fernanda Rodrigues Nascimento2,Marisa Alves Nogueira Diaz2

1 Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais 31270-901, Brazil

2 Department of Biochemistry and Molecular Biology, Universidade Federal de Viçosa, Viçosa, Minas Gerais 36570-900, Brazil

Abstract

This chapter reports advances in synthetic methodologies employing chiral auxiliaries for the stereoselective synthesis of biologically active natural molecules. Derivatives of naturally occurring compounds such as amino acids, carbohydrates, and terpenes, chiral auxiliaries have been described as an essential aid for the construction of highly complex molecules. Among these auxiliaries, we highlight those of Evans, Corey, Yamada, Enders, Oppolzer, Kunz, Meyers, and Schöllkopf, whose contributions led to a remarkable progress in asymmetric synthesis in the last decades and continue to bring advances until the present day.

Keywords: Asymmetric Synthesis, Biologically Active Compounds, Chiral Auxiliaries, Corey’s Chiral Auxiliary, Evans’ Oxazolidinones, Enders, Kunz, Meyers, Oppolzer, Schöllkopf, Yamada.

*Corresponding author Gaspar Diaz-Muñoz: Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais 31270-901, Brazil; Tel: [phone]; Fax: [phone]; E-mail: [email protected]