Synthesis of Heterocycles by Metathesis Reactions PDF
Preview Synthesis of Heterocycles by Metathesis Reactions
Topics in Heterocyclic Chemistry 47 Series Editors: Bert Maes · Janine Cossy · Slovenko Polanc Joëlle Prunet Editor Synthesis of Heterocycles by Metathesis Reactions 47 Topics in Heterocyclic Chemistry SeriesEditors: Bert Maes, Antwerp, Belgium Janine Cossy, Paris, France Slovenko Polanc, Ljubljana, Slovenia Editorial Board: D. Enders, Aachen, Germany S.V. Ley, Cambridge, UK G. Mehta, Bangalore, India R. Noyori, Hirosawa, Japan L.E. Overmann, Irvine, CA, USA A. Padwa, Atlanta, GA, USA Aims and Scope The series Topics in Heterocyclic Chemistry presents critical reviews on present andfuturetrendsintheresearchofheterocycliccompounds.Overallthescopeisto covertopicsdealingwithallareaswithinheterocyclicchemistry,bothexperimental andtheoretical,ofinteresttothegeneralheterocyclicchemistrycommunity. The series consists of topic related volumes edited by renowned editors with contributionsofexpertsinthefield. More information about this series at http://www.springer.com/series/7081 Joe¨lle Prunet Editor Synthesis of Heterocycles by Metathesis Reactions With contributions by (cid:1) (cid:1) (cid:1) (cid:1) M. Bassetti J.F. Bower P. Compain A. D’Annibale (cid:1) (cid:1) (cid:1) (cid:1) A. Gradillas P.R. Hanson D. Hazelard S. Javed (cid:1) (cid:1) (cid:1) (cid:1) J.H. Jun A. Letort D.M. Lindsay C.N. Ndi J. Pe´rez-Castells (cid:1) J. Prunet (cid:1) N.J. Race (cid:1) D.T.S. Rijkers (cid:1) G. Vincent Editor Joe¨llePrunet SchoolofChemistry UniversityofGlasgow Glasgow UnitedKingdom ISSN1861-9282 ISSN1861-9290 (electronic) TopicsinHeterocyclicChemistry ISBN978-3-319-39939-3 ISBN978-3-319-39941-6 (eBook) DOI10.1007/978-3-319-39941-6 LibraryofCongressControlNumber:2016957352 ©SpringerInternationalPublishingSwitzerland2017 Thisworkissubjecttocopyright.AllrightsarereservedbythePublisher,whetherthewholeorpartof the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilarmethodologynowknownorhereafterdeveloped. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publicationdoesnotimply,evenintheabsenceofaspecificstatement,thatsuchnamesareexempt fromtherelevantprotectivelawsandregulationsandthereforefreeforgeneraluse. Thepublisher,theauthorsandtheeditorsaresafetoassumethattheadviceandinformationinthis book are believed to be true and accurate at the date of publication. Neither the publisher nor the authors or the editors give a warranty, express or implied, with respect to the material contained hereinorforanyerrorsoromissionsthatmayhavebeenmade. Printedonacid-freepaper ThisSpringerimprintispublishedbySpringerNature TheregisteredcompanyisSpringerInternationalPublishingAGSwitzerland Foreword Onewouldbehardpressedtofindasetofchemicaltransformationsthatcandeliver heterocyclic structures with a wider scope than catalytic olefin metathesis. It is therefore of little surprise that in countless academic laboratories and in many programs in industry, whether it is to develop a potent therapeutic, a tantalizing fragrance, orapolymeric structure thathas aparticularsetofproperties,catalytic olefinand/oralkynemetathesisistheperennialfavorite.Inagreatnumberofcases, thetargetedmoleculesarecyclicstructuresthatcontainoneormoreheteroatoms, whichrenderthepresentcollectionofarticlesofexceptionalvalue. First, there is a concise overview of some of the more important fundamental aspectsofmetathesisreactionsthatinvolvealkenyland/oralkynylsubstrates.This is the most welcome beginning because it will appeal especially to the younger scientistsforwhomthisbookwillserveastheirintroductiontodifferentvarietiesof metathesis reactions. The hardened chemist with many years of experience may skipthisinitialtreatmentbuthardlywhatcomesafterward. We then have the article by Bower and Race who expertly demonstrate that a myriadofheteroaromaticstructures–the“breadandbutter”ofmedicinalchemistry – can be accessed by a variety of olefin metathesis transformations or one might consideranenyneastheoptimalstartingpoint.ThechapterbyLindseyrevealshow catalyticring-closingmetathesis(RCM)canallowoneassemble,withremarkable efficiency,beautifulrowsoffive-,six-,seven-,andnine-memberedringethersthat are referred to as gambieric acids A–D or ciguatoxin CTX3C. Then there is kendomycinandneopeltolide–smallertargetsnodoubtbutonesthatbringtothe tabletheirownuniqueflavorofdifficultiesandchallenges. The ensuing chapters by Bassetti and D’Annibale and then by Compain and Hazelard offer different views of a somewhat different landscape, one that deals less with total synthesis and more with how one might prepare most efficiently some of the more commonly occurring medium-sized lactones and nitrogen- containingrings.Thespecialsignificanceofcyclicaminesandrelatedderivatives isunderscoredbyVincentinthesubsequentoverview,showingushowonemight go about designing pathways that lead to lactam structures. These are routes that v vi Foreword could include a ring-closing alkene metathesis, a ring-closing enyne metathesis, a ringrearrangementmetathesis,oracrossmetathesis(CM)reaction. Andthenthereareallthosebeautifullarge-ringheterocyclicstructuresthatcan bepreparedbyametathesis-typeprocess.Therearetwowell-writtenchaptersthat coverthiscrucialtopic.ThefirstisbyRijkerswhotreatsuswithanaccountofthe emergingfieldofmacrocyclicpeptidesynthesis;herewecanreadabouthowalkene metathesis is being utilized in the design of amino acid-based therapeutic candidates. What follows is an article by Gradillas and Pe´rez-Castells vis-a`-vis thestateoftheartinpreparationofcomplexmacrocyclesthroughalkeneoralkyne metathesis. These contributors make it clear that metathesis-based catalytic strategies have allowed chemists to reach their final targets through remarkably briefsequences. Thelastpartofthestory,pennedbyHanson,Jun,Javed,andNditakesusona tour of cyclic structures that contain some of the less encountered – but equally important–heteroatoms:phosphorous,sulfur,silicon,boron,andselenium.Wesee that catalytic metathesis strategies may be utilized to access some intriguing structureswithplentyofuntappedpotential. What I find most appealing about this book, other than the fact that it contains countless pieces of useful information, is the exciting number of yet unaddressed issuesthatwouldrenderolefin,enyne,oralkynemetathesismorepowerfulstill.We have come a long way no doubt, but we have yet a considerable distance to go.Whatliesaheadislikelytobeamorearduousroad;theproblemsthatremain arecompellingbutalsoprobablyfarmoredemandingtosolve. MerkertChemistryCenter,BostonCollege,USA AmirH.Hoveyda Preface Thisvolumeisdedicatedtothesynthesesofheterocyclesthatinvolveametathesis reaction as a key step, but not necessarily as the ring-forming step. The different chapters are not comprehensive reviews, but outline recent progress toward the synthesisofspecificheterocycleswhilegivingthereaderinsightsofthefactorsthat governtheformationoftheseheterocycles. Theintroductionentitled“MetathesisReactions:GeneralConsiderations,”writ- tenbyAure´lienLetortandmyself,presentsthedifferentkindsofalkene,enyne,and alkynemetathesisreactionsandtheassociatedmechanisms. In the first chapter “Synthesis of Heteroaromatic Compounds by Alkene and Enyne Metathesis,” Nicholas J.Race andJohnF.Bower describethe synthesis of aromatic heterocycles such as furans and pyrroles, pyridones and pyridines, and pyridazinones and pyridazines, using ring-closing metathesis (RCM) or cross metathesis(CM)reactions. The chapter entitled “The Synthesis of Cyclic Ether-Containing Natural and Non-naturalProductsbyMetathesisReactions,”writtenbyDavidLindsay,focuses ontheuseofmetathesisintotalsynthesis,sincethemethodologicalaspectsofthis topichavebeenveryrecentlyreviewedinanotherbookofthisseries. Mauro Bassetti and Andrea D’Annibale, in the chapter entitled “Metathetic Synthesis of Common and Medium-Sized Lactones: The State of the Art,” cover the synthesis of 5- to 11-membered lactones, focusing on the most recent publications. For each ring size, they distinguish the acrylate approach, where one of the alkenes participating in the RCM reaction is conjugated to the ester, fromtheotherpossibleringformations. The fourth chapter entitled “Synthesis of Amine-Containing Heterocycles by Metathesis Reactions: Recent Advances and Opportunities” by Philippe Compain and Damien Hazelard highlights the difficulties of metathesis reactions in the presence of amines and details the steric and electronic parameters that prevent thedeleteriouscoordinationoftheaminogrouptothecatalystmetalcenter. Guillaume Vincent describes in the fifth chapter the “Synthesis of Lactams by Metathesis Reactions.” This chapter is structured according to the metathesis vii viii Preface reaction employed, RCM, CM, ring-closing enyne metathesis (RCEYM), or ring-rearrangement metathesis (RRM) and discusses the various parameters that governthemetathesisreactions. Thefollowingchapter,writtenbyDirkT.S.Rijkers,reviewsrecentadvanceson the “Synthesis of Cyclic Peptides and Peptidomimetics by Metathesis Reactions” andshowstheprominentroleofmetathesisreactionsin,interalia,alternativesfor disulfide bridge formation, stabilization of peptide secondary structures, and a-helixstabilization. Intheseventhchapterentitled“SynthesisofMacrocyclesotherthanPeptidesby Metathesis,” Ana Gradillas and Javier Pe´rez-Castells discuss the conditions that mayfavortheformationofthesemacrocycles.Theythenpresentrecentsyntheses ofnaturalmacrocyclicheterocyclesaccordingtoabiogeneticclassification,aswell asnonnaturalproductsincludingmacromoleculesforsupramolecularchemistry. The last chapter “Synthesis of P-, S-, Si-, B-, and Se-Heterocycles via Ring- Closing Metathesis,” writtenbyJungHo Jun,SalimJaved,CorneliusN.Ndi,and Paul R. Hanson, deals with the synthesis of less common heterocycles. These heterocycles are synthesized as a goal per se, or the heterocyclic element is part of a temporary tether that facilitates difficult intermolecular olefin formations as wellasdirectstheirstereoselectiveoutcome. Iwouldliketothankalltheauthorswhohaveparticipatedinthisbookfortheir exceptional work. I am also grateful to Janine Cossy for having given me the opportunity to edit this volume, and I hope it will be a useful support for the chemistsinvolvedinheterocyclicsynthesis. Glasgow,Scotland Joe¨llePrunet Contents IntroductiontoVolume:MetathesisReactions:GeneralConsiderations Aure´lienLetortandJoe¨llePrunet SynthesisofHeteroaromaticCompoundsbyAlkeneandEnyne Metathesis. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 NicholasJ.RaceandJohnF.Bower TheSynthesisofCyclicEther-ContainingNaturalandNon-natural ProductsbyMetathesisReactions. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 33 DavidM.Lindsay MetatheticSynthesisofCommonandMedium-SizedLactones: TheStateoftheArt. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 57 MauroBassettiandAndreaD’Annibale SynthesisofAmine-ContainingHeterocyclesbyMetathesisReactions: RecentAdvancesandOpportunities. . . . . . . . . . . . . . . . . . . . . . . . . . . 111 PhilippeCompainandDamienHazelard SynthesisofLactamsbyMetathesisReactions. . . . . . . . . . . .. . . . . . . . 155 GuillaumeVincent SynthesisofCyclicPeptidesandPeptidomimeticsbyMetathesis Reactions. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 191 DirkT.S.Rijkers SynthesisofMacrocyclesOtherthanPeptidesbyMetathesis. . . . . . . . 245 AnaGradillasandJavierPe´rez-Castells SynthesisofP-,S-,Si-,B-,andSe-HeterocyclesviaRing-Closing Metathesis. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 319 JungHoJun,SalimJaved,CorneliusN.Ndi,andPaulR.Hanson ix
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