Modern Tools for the Synthesis of Complex Bioactive Molecules PDF
Preview Modern Tools for the Synthesis of Complex Bioactive Molecules
MODERN TOOLS FOR THE SYNTHESIS OF COMPLEX BIOACTIVE MOLECULES MODERN TOOLS FOR THE SYNTHESIS OF COMPLEX BIOACTIVE MOLECULES Edited by JANINE COSSY STELLIOS ARSENIYADIS Copyright(cid:2)2012byJohnWiley&Sons,Inc.Allrightsreserved. PublishedbyJohnWiley&Sons,Inc.,Hoboken,NewJersey. PublishedsimultaneouslyinCanada. Nopartofthispublicationmaybereproduced,storedinaretrievalsystem,ortransmittedinanyform orbyanymeans,electronic,mechanical,photocopying,recording,scanning,orotherwise,except aspermittedunderSection107or108ofthe1976UnitedStatesCopyrightAct,withouteitherthe priorwrittenpermissionofthePublisher,orauthorizationthroughpaymentoftheappropriateper-copy feetotheCopyrightClearanceCenter,Inc.,222RosewoodDrive,Danvers,MA01923,(978)750-8400, fax(978)750-4470,oronthewebatwww.copyright.com.RequeststothePublisherfor permissionshouldbeaddressedtothePermissionsDepartment,JohnWiley&Sons,Inc., 111RiverStreet,Hoboken,NJ07030,(201)748-6011,fax(201)748-6008,oronlineat http://www.wiley.com/go/permission. 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ISBN978-0-470-61618-5(hardback) PrintedintheUnitedStatesofAmerica 10 9 8 7 6 5 4 3 2 1 CONTENTS FOREWORD vii PREFACE ix CONTRIBUTORS xi CHAPTER1 C–HFUNCTIONALIZATION:ANEWSTRATEGYFOR THESYNTHESISOFBIOLOGICALLYACTIVENATURALPRODUCTS 1 SophieRousseaux,BenoˆıtLie´gault,andKeithFagnou CHAPTER2 THENEGISHICROSS-COUPLINGINTHESYNTHESIS OFNATURALPRODUCTSANDBIOACTIVEMOLECULES 33 EvelinaColacino,JeanMartinez,andFre´de´ricLamaty CHAPTER3 METAL-CATALYZEDC–HETEROATOM CROSS-COUPLINGREACTIONS 77 RenataMarciadeFigueiredo,JeanMarcCampagne,andDamienPrim CHAPTER4 GOLDENOPPORTUNITIESINTHESYNTHESISOFNATURAL PRODUCTSANDBIOLOGICALLYACTIVECOMPOUNDS 111 FabienGagosz CHAPTER5 METATHESIS-BASEDSYNTHESISOFCOMPLEXBIOACTIVES 155 Jean-AlexandreRichard,SinYeeNg,andDavidY.-K.Chen CHAPTER6 ENANTIOSELECTIVEORGANOCATALYSIS:APOWERFUL TOOLFORTHESYNTHESISOFBIOACTIVEMOLECULES 189 MitsuruShojiandYujiroHayashi CHAPTER7 ASYMMETRICPHASE-TRANSFERCATALYSIS 213 SeijiShirakawa,ShinA.Moteki,andKeijiMaruoka CHAPTER8 REARRANGEMENTSINNATURALPRODUCTSYNTHESIS 243 Jose´ Marco-ContellesandElenaSoriano v vi CONTENTS CHAPTER9 DOMINOREACTIONSINTHEENANTIOSELECTIVESYNTHESIS OFBIOACTIVENATURALPRODUCTS 271 LutzF.Tietze,ScottG.Stewart,andAlexanderDu¨fert CHAPTER10 FLUOROUSLINKER-FACILITATEDSYNTHESISOFBIOLOGICALLY INTERESTINGMOLECULES 335 WeiZhang CHAPTER11 THEEVOLUTIONOFIMMOBILIZEDREAGENTSANDTHEIR APPLICATIONINFLOWCHEMISTRYFORTHESYNTHESIS OFNATURALPRODUCTSANDPHARMACEUTICALCOMPOUNDS 359 RebeccaM.Myers,KimberleyA.Roper,IanR.Baxendale, andStevenV.Ley CHAPTER12 SYNTHETICAPPROACHESTOBIOACTIVECARBOHYDRATES 395 XavierGuinchard,Se´bastienPicard,andDavidCrich CHAPTER13 AMMONIUMYLIDESASBUILDINGBLOCKSFOR ALKALOIDSYNTHESIS 433 ScottBurandAlbertPadwa CHAPTER14 PRECURSOR-DIRECTEDBIOSYNTHESISOFPOLYKETIDE ANDNONRIBOSOMALPEPTIDENATURALPRODUCTS 485 ColinJ.B.HarveyandChaitanKhosla CHAPTER15 TARGET-ORIENTEDANDDIVERSITY-ORIENTED ORGANICSYNTHESIS 513 Raphae¨lRodriguez CHAPTER16 DNAASATOOLFORMOLECULARDISCOVERY 539 MichaelSmietana,Jean-JacquesVasseur,JanineCossy, andStelliosArseniyadis INDEX 557 FOREWORD Thanks toarichevolutionover thepast century,organicsynthesishas allowed the preparationofcomplexmoleculesandnewmaterialswithincredibleproperties.One ofthemainchallengesistofindnewandbetterwaystoaccesscomplexmoleculesin anatom-andstep-economicalprocess(ASEP).Tothisend,novelandhighlyselective reagents and chemical reactionshavebeen developed. This book,ModernTools fortheSynthesisofComplexBioactive Molecules, contains16chapters,withparticularemphasisgiventoorganic,organometallic,and bio-orientedprocesses.Thefirstpartisdirectedtowardthedevelopmentofcatalytic systemsforC–Hfunctionalizations,cross-couplings,andreactionsinvolvingorgano- metalliccatalysts,organocatalysts,andbioorganiccatalysts.Thesecondpartcovers someofthemostrecentASEPmethodsdevelopedsofar,suchasdominoreactions andrearrangements.Thelasttwopartsofthebookarededicatedtotheuseofefficient tools for the synthesis of complex bioactives, in particular, carbohydrates and alkaloids, as well as to new techniques, such as the use of fluorous tags, flow chemistry, engineered biosynthesis, target- and diversity-oriented synthesis, and DNA-based asymmetric catalysis. Thisbookisanexcellentsourceofinspirationforthoseplanningthesynthesis ofcomplexmoleculesinthemostefficientmanner,forgettingahintonhowtosolvea specificsyntheticproblem,orsimplyforhavingfundiscoveringnewchemistriesand elaborating future chemical tools. E. Negishi vii PREFACE Inaworldwhereatom-,step-,redox-,andpot-economyhavebecomesomeofthemost important challenges in syntheticorganic chemistry, the development ofinnovative andsyntheticallyusefultoolshasmorethannottransfiguredthewaychemistsdevise theirsynthesesofcomplexbiologicallyactivemolecules.Thus,theideabehindthis book was to emphasize the impact of modern synthetic tools on the synthesis of complexbiologicallyactivecompounds,andshowhowtheyhaveprovidednewand elegantsolutionstomanysyntheticpuzzles.Inthiscontext,wedecidedtodedicatethe firstpartofthisbooktomoderncatalysiswithaspecialemphasisgiventovariouskey transformationssuchasC–Hfunctionalizations(Chapter1,S.Rousseaux,B.Lie´gault, andK.Fagnou),cross-couplings(Chapter2,E.Colacino,J.Martinez,andF.Lamaty and Chapter 3, R. Marcia de Figueiredo, J.-M. Campagne, and D. Prim), gold- catalyzedreactions (Chapter 4,F. Gagosz), metathesis-based syntheses (Chapter 5, J.-A. Richard, S. Y. Ng, and D. Y.-K. Chen), and asymmetric organocatalysis (Chapter6,M.ShojiandY.HayashiandChapter7,S.Shirakawa,S.A.Moteki,and K.Maruoka).Thesecondpartofthebookprovidesabroadcoverageofsomeofthe mostelegantandeco-compatibletransformationsdevelopedsofar,suchasrearrange- ments (Chapter 8, J. Marco-Contelles and E. Soriano) and domino reactions (Chapter 9, L. F. Tietze, S. G. Stewart, and A. D€ufert). The third part of the book is dedicated to the development of specific tools for the synthesis of carbohydrates (Chapter12,X.Guinchard,S.Picard,andD.Crich)andalkaloids(Chapter13,S.Bur andA.Padwa),whilethefourthpartunveilssomeofthemostrecenttechniques,such as the use of fluorous tags (Chapter 10, W. Zhang), flow chemistry (Chapter 11, R.M.Myers,K.A.Roper,I.R.Baxendale,andS.V.Ley)andengineeredbiosynthesis (Chapter14,C.J.B.HarveyandC.Khosla).Finally,thelasttwochaptersofthisbook are dedicated to two prospective methods, namely, target- and diversity-oriented organicsynthesis(Chapter15,R.Rodriguez)andtheuseofDNA-basedasymmetric catalysis(Chapter16,M.Smietana,J.-J.Vasseur,J.Cossy,andS.Arseniyadis)thatare particularlypromisingtoolsforthesynthesisofcomplexbioactivemolecules. Wewouldliketowarmlythankalltheauthorsfortheirenthusiasm,patience, professionalism,andmostofall,theirparticularlydidacticanddetailedcontributions. We also would like to thank the team at John Wiley & Sons, especially Anita Lekhwani,SanchariSil,andAngiolineLoredo,fortheirhelpfulassistanceduringthe entire preparation ofthis book. Finally,wehopeyouwillenjoyreadingthisbookasmuchaswehaveenjoyed preparingit.Webelieveitwillbeavaluablesourceofinformationforbothacademic andindustrialresearchers,aswellastoundergraduateandgraduatestudentsallover theworld. Janine Cossy andStellios Arseniyadis ix CONTRIBUTORS StelliosArseniyadis, LaboratoiredeChimieOrganique,UMR7084CNRSESPCI ParisTech, Paris,France IanR.Baxendale, DepartmentofChemistry,UniversityofCambridge,Cambridge, United Kingdom Scott Bur, Department of Chemistry, Emory University, Atlanta, Georgia,USA JeanMarcCampagne, InstitutCharlesGerhardtMontpellier,UMR5253CNRS- UM2-UM1-ENSCM,EcoleNationaleSupe´rieuredeChimie,Montpellier,France David Y.-K. Chen, Department of Chemistry, Seoul National University, Seoul, SouthKorea EvelinaColacino, InstitutdesBiomole´culesMaxMousseron,Universite´Montpel- lier 2,Montpellier, France Janine Cossy, Laboratoire de Chimie Organique, UMR 7084 CNRS ESPCI ParisTech, Paris,France DavidCrich, InstitutdeChimiedesSubstancesNaturelles,Gif-sur-Yvette,France RenataMarciadeFigueiredo, InstitutCharlesGerhardtMontpellier,UMR5253 CNRS-UM2-UM1-ENSCM,EcoleNationaleSupe´rieuredeChimie,Montpellier, France AlexanderDu€fert, Institutf€urOrganischeundBiomolekulareChemie,Universit€at G€ottingen,G€ottingen, Germany Keith Fagnou, Department of Chemistry, University of Ottawa, Ottawa, Ontario, Canada Fabien Gagosz, Laboratoire de Synthe`se Organique, UMR 7652 CNRS Ecole Polytechnique, Palaiseau, France Xavier Guinchard, Institut de Chimie des Substances Naturelles, Gif-sur-Yvette, France Colin J. B. Harvey, Department of Chemistry, Chemical Engineering, and Bio- chemistry, Stanford University, Stanford,California,USA YujiroHayashi, DepartmentofIndustrialChemistry,TokyoUniversityofScience, Tokyo,Japan ChaitanKhosla, DepartmentofChemistry,ChemicalEngineering,andBiochem- istry, Stanford University,Stanford,California, USA xi xii CONTRIBUTORS Fre´de´ricLamaty, InstitutdesBiomole´culesMaxMousseron,Universite´Montpel- lier 2, Montpellier,France Steven V. Ley, Department of Chemistry, University of Cambridge, Cambridge, United Kingdom Beno^ıtLie´gault, DepartmentofChemistry,UniversityofOttawa,Ottawa,Ontario, Canada Jose´Marco-Contelles, LaboratoriodeQu(cid:2)ımicaMe´dicayComputacional,Instituto deQu(cid:2)ımica Org(cid:2)anicaGeneral, Madrid,Spain JeanMartinez, InstitutdesBiomole´culesMaxMousseron,Universite´Montpellier 2,Montpellier, France KeijiMaruoka, DepartmentofChemistry,KyotoUniversity,Sakyo,Kyoto,Japan ShinA.Moteki, DepartmentofChemistry,KyotoUniversity,Sakyo,Kyoto,Japan Rebecca M. Myers, Department of Chemistry, University of Cambridge, Cambridge,United Kingdom Sin Yee Ng, Department of Chemistry, Seoul National University, Seoul, South Korea AlbertPadwa, DepartmentofChemistry,EmoryUniversity,Atlanta,Georgia,USA Se´bastien Picard, Institut de Chimie des Substances Naturelles, Gif-sur-Yvette, France Damien Prim, Universite´ Versailles-St-Quentin-en-Yvelines, Institut Lavoisier de Versailles UMR CNRS 8180, Versailles,France Jean-Alexandre Richard, Department of Chemistry, Seoul National University, Seoul, South Korea Rapha€elRodriguez, DepartmentofChemistry,CambridgeUniversity,Cambridge, United Kingdom Kimberley A. Roper, Department of Chemistry, University of Cambridge, Cambridge,United Kingdom Sophie Rousseaux, Department of Chemistry, University of Ottawa, Ottawa, Ontario, Canada SeijiShirakawa, DepartmentofChemistry,KyotoUniversity,Sakyo,Kyoto,Japan Mitsuru Shoji, Department ofIndustrialChemistry,TokyoUniversityofScience, Tokyo,Japan MichaelSmietana, InstitutdesBiomole´culesMaxMousseron,UMR5247CNRS, Universite´ de Montpellier 1 et 2, Montpellier,France Elena Soriano, Laboratorio de Qu(cid:2)ımica Me´dica y Computacional, Instituto de Qu(cid:2)ımicaOrg(cid:2)anica General, Madrid, Spain CONTRIBUTORS xiii Scott G. Stewart, Institut f€ur Organische und Biomolekulare Chemie, Universit€at G€ottingen,G€ottingen, Germany Lutz F. Tietze, Institut f€ur Organische und Biomolekulare Chemie, Universit€at G€ottingen,G€ottingen, Germany Jean-Jacques Vasseur, Institut des Biomole´cules Max Mousseron, UMR 5247 CNRS, Universite´ de Montpellier 1 et 2, Montpellier,France Wei Zhang, Department of Chemistry, University of Massachusetts, Boston, Massachusetts, USA
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