Natural Product Synthesis I: Targets, Methods, Concepts (Topics in Current Chemistry 243)

250 Pages·2005·3.77 MB·English

by  Johann H. Mulzer

243
Topics in Current Chemistry
Editorial Board:
A. de Meijere · K.N. Houk · H. Kessler · J.-M. Lehn · S.V. Ley
S.L. Schreiber · J. Thiem · B.M. Trost · F. V(cid:1)gtle · H. Yamamoto
Topics in Current Chemistry
Recently Published and Forthcoming Volumes
AnionSensing NaturalProductSynthesisI
VolumeEditor:Stibor,I. VolumeEditor:Mulzer,J.H.
Vol.255,2005 Vol.243,2004
OrganicSolidStateReactions ImmobilizedCatalysts
VolumeEditor:Toda,F. VolumeEditor:Kirschning,A.
Vol.254,2005 Vol.242,2004
DNABindersandRelatedSubjects TransitionMetalandRareEarth
VolumeEditors:Waring,J.,Chaires,J.B. CompoundsIII
Vol.253,2005 VolumeEditor:Yersin,H.
Vol.241,2004
ContrastAgentsII
VolumeEditor:Krause,W. TheChemistryofPheromones
Vol.252,2005 andOtherSemiochemicalsII
VolumeEditor:Schulz,S.
ChalcogenocarboxylicAcidDerivatives Vol.240,2004
VolumeEditor:Kato,S.
Vol.251,2005 TheChemistryofPheromones
andOtherSemiochemicalsI
NewAspectsinPhosphorusChemistryV VolumeEditor:Schulz,S.
VolumeEditor:Majoral,J.-P. Vol.239,2004
Vol.250,2005
OrotidineMonophosphateDecarboxylase
TemplatesinChemistryII VolumeEditors:Lee,J.K.,Tantillo,D.J.
VolumeEditors:Schalley,C.A.,V(cid:1)gtle,F., Vol.238,2004
D(cid:1)tz,K.-H.
Vol.249,2005 Long-RangeChargeTransferinDNAII
VolumeEditor:Schuster,G.B.
TemplatesinChemistryI Vol.237,2004
VolumeEditors:Schalley,C.A.,V(cid:1)gtle,F.,
D(cid:1)tz,K.-H. Long-RangeChargeTransferinDNAI
Vol.248,2005 VolumeEditor:Schuster,G.B.
Vol.236,2004
Collagen
VolumeEditors:Brinckmann,J., SpinCrossoverinTransitionMetal
Notbohm,H.,M(cid:2)ller,P.K. CompoundsIII
Vol.247,2005 VolumeEditors:G(cid:2)tlich,P.,Goodwin,H.A.
Vol.235,2004
NewTechniquesinSolid-StateNMR
VolumeEditor:Klinowski,J. SpinCrossoverinTransitionMetal
Vol.246,2005 CompoundsII
VolumeEditors:G(cid:2)tlich,P.,Goodwin,H.A.
FunctionalMolecularNanostructures Vol.234,2004
VolumeEditor:Schl(cid:2)ter,A.D.
Vol.245,2004 SpinCrossoverinTransition
MetalCompoundsI
NaturalProductSynthesisII VolumeEditors:G(cid:2)tlich,P.,Goodwin,H.A.
VolumeEditor:Mulzer,J.H. Vol.233,2004
Vol.244,2004
Natural Product Synthesis I
Targets, Methods, Concepts
Volume Editor: Johann H. Mulzer
With contributions by
T. Bach · R. Bandichhor · B. Basler · S. Brandes · M. Hiersemann
H. Helmboldt · B. Nosse · O. Reiser · E. Ruijter · M. Sefkow
A. Spiegel · L.A. Wessjohann
TheseriesTopicsinCurrentChemistrypresentscriticalreviewsofthepresentandfuturetrendsin
modernchemicalresearch.Thescopeofcoverageincludesallareasofchemicalscienceincluding
theinterfaceswithrelateddisciplinessuchasbiology,medicineandmaterialsscience.Thegoalof
eachthematicvolumeistogivethenonspecialistreader,whetherattheuniversityorinindustry,a
comprehensiveoverviewofanareawherenewinsightsareemergingthatareofinteresttoalarger
scientificaudience.
Asarule,contributionsarespeciallycommissioned.Theeditorsandpublisherswill,however,always
bepleasedtoreceivesuggestionsandsupplementaryinformation.PapersareacceptedforTopicsin
CurrentChemistryinEnglish.
InreferencesTopicsinCurrentChemistryisabbreviatedTopCurrChemandiscitedasajournal.
VisittheTCCcontentatspringerlink.com
LibraryofCongressControlNumber:2004112161
ISSN0340-1022
ISBN3-540-21125-XSpringerBerlinHeidelbergNewYork
DOI10.1007/b10390
Thisworkissubjecttocopyright.Allrightsarereserved,whetherthewholeorpartofthematerial
isconcerned,specificallytherightsoftranslation,reprinting,reuseofillustrations,recitation,broad-
casting,reproductiononmicrofilmsorinanyotherways,andstorageindatabanks.Duplicationof
thispublicationor partsthereofis only permittedunder theprovisionsoftheGerman Copyright
LawofSeptember9,1965,initscurrentversion,andpermissionforusemustalwaysbeobtained
fromSpringer-Verlag.ViolationsareliabletoprosecutionundertheGermanCopyrightLaw.
SpringerisapartofSpringerScience+BusinessMedia
springeronline.com
(cid:3)Springer-VerlagBerlinHeidelberg2005
PrintedinGermany
Theuseofgeneraldescriptivenames,registerednames,trademarks,etc.inthispublicationdoesnot
imply,evenintheabsenceofaspecificstatement,thatsuchnamesareexemptfromtherelevantpro-
tectivelawsandregulationsandthereforefreeforgeneraluse.
Coverdesign:K(cid:2)nkelLopka,Heidelberg/design&productionGmbH,Heidelberg
Typesetting:St(cid:2)rtzGmbH,W(cid:2)rzburg
Printedonacid-freepaper 02/3020ra–543210
Volume Editor
Professor Dr.JohannMulzer
Institutf(cid:2)rOrganischeChemie
Universit(cid:4)tWien
W(cid:4)hringerstr.38
1090Wien,Austria
[email protected]
Editorial Board
Prof.Dr.ArmindeMeijere Prof.K.N.Houk
Institutf(cid:2)rOrganischeChemie DepartmentofChemistry
derGeorg-August-Universit(cid:4)t andBiochemistry
Tammannstraße2 UniversityofCalifornia
37077G(cid:1)ttingen,Germany 405HilgardAvenue
E-mail:[email protected] LosAngeles,CA90024-1589,USA
E-mail:[email protected]
Prof.Dr.HorstKessler
Prof.Jean-MarieLehn
Institutf(cid:2)rOrganischeChemie
TUM(cid:2)nchen InstitutdeChimie
Lichtenbergstraße4 Universit(cid:5)deStrasbourg
85747Garching,Germany 1rueBlaisePascal,B.P.Z296/R8
E-mail:[email protected] 67008StrasbourgCedex,France
E-mail:[email protected]
Prof.StevenV.Ley
Prof.StuartL.Schreiber
UniversityChemicalLaboratory
ChemicalLaboratories
LensfieldRoad
HarvardUniversity
CambridgeCB21EW,GreatBritain
12OxfordStreet
E-mail:[email protected]
Cambridge,MA02138-2902,USA
E-mail:[email protected]
Prof.Dr.JoachimThiem
Institutf(cid:2)rOrganischeChemie Prof.BarryM.Trost
Universit(cid:4)tHamburg DepartmentofChemistry
Martin-Luther-King-Platz6 StanfordUniversity
20146Hamburg,Germany Stanford,CA94305-5080,USA
E-mail:[email protected] E-mail:[email protected]
Prof.Dr.FritzV(cid:1)gtle Prof.HisashiYamamoto
ArthurHollyComptonDistinguished
Kekul(cid:5)-Institutf(cid:2)rOrganischeChemie
Professor
undBiochemiederUniversit(cid:4)tBonn
DepartmentofChemisty
Gerhard-Domagk-Straße1
TheUniversityofChicago
53121Bonn,Germany
5735SouthEllisAvenue
E-mail:[email protected]
Chicago,IL60637
733-702-5059,USA
E-mail:[email protected]
Topics in Current Chemistry
Also Available Electronically
ForallcustomerswhohaveastandingordertoTopicsinCurrentChemistry,
weoffertheelectronicversionviaSpringerLinkfreeofcharge.Please
contactyourlibrarianwhocanreceiveapasswordforfreeaccesstothefull
articlesby registeringat:
springerlink.com
Ifyoudonothaveasubscription,youcanstillview thetablesofcontentsof
thevolumesandtheabstractofeacharticlebygoingtotheSpringerLink
Homepage,clickingon“BrowsebyOnlineLibraries”,then“Chemical
Sciences”,andfinallychooseTopicsinCurrentChemistry.
Youwillfindinformationaboutthe
–EditorialBoard
–AimsandScope
–InstructionsforAuthors
–SampleContribution
atspringeronline.comusingthesearchfunction.
Preface
From its early days, the total synthesis of complex molecules, especially
those that are natural products, has been the king(cid:1)s discipline in organic
chemistry. The reasons for this are manifold: the challenge lying in a novel
and intricate molecular architecture or the difficulty encountered when iso-
lating the substance from its natural sources, or the possibility of finding a
widetestgroundforestablishedmethodologyor theincentivetoinventnew
methodology when the old one has failed, or simply the art and elegance
whichissotypicalofatrulyefficientsyntheticsequence.Inanycase,every-
body will agree that total synthesis is the best way to train young chemists
andtopreparethemforanykindoflateremployment.
Inthesetwovolumes,thecontributionsofanumberoforganicsyntheticche-
mists from the German speaking area have been collected. It is the hope of the
authorsandtheeditorthatthesearticles,whichhighlightallthevariousaspects
oforganicsynthesis,willprovidenotonlyaninsightintothebasicstrategyand
tacticsbutalsothepurposeoforganicsyntheses.
Vienna,September2004 JohannMulzer

Contents
TotalSynthesesofKelsoeneandPreussin
B.Basler·S.Brandes·A.Spiegel·T.Bach......................... 1
ParaconicAcids–TheNaturalProductsfromLichenSymbiont
R.Bandichhor·B.Nosse·O.Reiser.............................. 43
RecentProgressintheTotalSynthesisofDolabellane
andDolastaneDiterpenes
M.Hiersemann·H.Helmboldt.................................. 73
StrategiesforTotalandDiversity-OrientedSynthesis
ofNaturalProduct(-Like)Macrocycles
L.A.Wessjohann·E.Ruijter .................................... 137
EnantioselectiveSynthesisofC(8)-HydroxylatedLignans:
EarlyApproachesandRecentAdvances
M.Sefkow................................................... 185
AuthorIndexVolumes201–243 ................................. 225
SubjectIndex ............................................... 237
Contents of Volume 244
Natural Product Synthesis II
Targets, Methods, Concepts
Volume Editor: J. Mulzer
ISBN 3-540-21124-1
MarineNaturalProductsfromPseudopterogorgiaElisabethae:
Structures,Biosynthesis,PharmacologyandTotalSynthesis
T.J.Heckrodt·J.Mulzer
RecentAdvancesinVinylogousAldolReactions
andTheirApplicationsintheSynthesesofNaturalProducts
M.Kalesse
MethanophenazineandOtherNaturalBiologicallyActivePhenazines
U.Beifuss·M.Tietze
Occurrence,BiologicalActivity,
andConvergentOrganometallicSynthesisofCarbazoleAlkaloids
H.-J.Knoelker
RecentAdvancesinCharge–AcceleratedAza-ClaisenRearrangements
U.Nubbemeyer
SyntheticStudiesonthePamamycinMacrodiolides
P.Metz