Synthesis of Heterocycles by Metathesis Reactions

410 Pages·2017·28.627 MB·English

by  Joëlle Prunet (eds.)

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
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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
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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