Alkaloid Synthesis

267 Pages·2012·3.13 MB·English

by  Mariko Kitajima

309
Topics in Current Chemistry
Editorial Board:
K.N. Houk C.A. Hunter M.J. Krische J.-M. Lehn
l l l
S.V. Ley M. Olivucci J. Thiem M. Venturi P. Vogel
l l l l
C.-H. Wong H. Wong H. Yamamoto
l l
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Alkaloid Synthesis
Volume Editor: Hans-Joachim Kno¨lker
With Contributions by
S.K. Adla (cid:1) M.G. Banwell (cid:1) I. Bauer (cid:1) H. Fujioka (cid:1) N.(Y.) Gao (cid:1)
T. Hudlicky (cid:1) M. Kitajima (cid:1) Y. Kita (cid:1) H.-J. Kno¨lker (cid:1) T. Lindel (cid:1)
N. Marsch (cid:1) U. Rinner (cid:1) B.D. Schwartz (cid:1) H. Takayama (cid:1) L.V. White
Editor
Prof.Dr.Hans-JoachimKno¨lker
DepartmentofChemistry
TechnicalUniversityDresden
Bergstraße66
01069Dresden
Germany
[email protected]
ISSN0340-1022 e-ISSN1436-5049
ISBN978-3-642-25528-1 e-ISBN978-3-642-25529-8
DOI10.1007/978-3-642-25529-8
SpringerHeidelbergDordrechtLondonNewYork
LibraryofCongressControlNumber:2011943173
#Springer-VerlagBerlinHeidelberg2012
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Editorial Board
Prof.Dr.KendallN.Houk Prof.Dr.StevenV.Ley
UniversityofCalifornia UniversityChemicalLaboratory
DepartmentofChemistryandBiochemistry LensfieldRoad
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DepartmentofChemistry Universita`diSiena
UniversityofSheffield DipartimentodiChimica
SheffieldS37HF,UnitedKingdom ViaADeGasperi2
c.hunter@sheffield.ac.uk 53100Siena,Italy
[email protected]
Prof.MichaelJ.Krische
Prof.Dr.JoachimThiem
UniversityofTexasatAustin
Institutfu¨rOrganischeChemie
Chemistry&Biochemistry Department
Universita¨tHamburg
1UniversityStationA5300
Martin-Luther-King-Platz6
AustinTX,78712-0165,USA
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[email protected]
[email protected]
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ISIS DipartimentodiChimica
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[email protected] [email protected]
vi EditorialBoard
Prof.Dr.PierreVogel Prof.Dr.HenryWong
LaboratoryofGlycochemistry TheChineseUniversityofHongKong
andAsymmetricSynthesis UniversityScienceCentre
EPFL–Ecolepolytechniquefe´derale DepartmentofChemistry
deLausanne Shatin,NewTerritories
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Preface
Naturalproductchemistryveryoftenstimulatesthedevelopmentofnovelpharma-
ceutical drugs. In fact, the vast majority of new lead structures in medicinal
chemistryarederivedfromframeworksofnaturallyoccurring compounds.Inthis
respect alkaloids lead the way and consequently a breathtaking progress in the
chemistryofalkaloidshastakenplaceoverthelastcentury.Especiallyoverthepast
decades, we can follow the evolution of numerous novel synthetic methodologies
for the total synthesis of biologically active alkaloids. Due to space limitation, of
course only a few aspects of some recent developments in “Alkaloid Synthesis”
couldbehighlightedinthepresentvolumeofTopicsinCurrentChemistry.Insix
contributions,differentresearchteamsfromAustria,Australia,Canada,Japanand
Germanyhavesummarizedimportantachievementsofthepastdecade.
Inthefirstchapter,MarikoKitajimaandHiromitsuTakayamafromtheGradu-
ate School of Pharmaceutical Sciences at Chiba University in Japan describe the
isolationandasymmetricsynthesisofLycopodiumalkaloids.Thefollowingchapter
isajointcontributionbyUweRinnerfromtheInstituteofOrganicChemistryatthe
University of Vienna in Austria and Tomas Hudlicky from the Department of
Chemistry and Centre of Biotechnology at Brock University in St. Catharines,
Canada. They discuss recent developments inthe synthesisof morphine alkaloids
and derivatives. Thomas Lindel, Nils Marsch and Santosh Kumar Adla from the
Institute of Organic Chemistry at the Technical University of Braunschweig de-
scribeimportantaspectsofindoleprenylationinalkaloidsynthesis.YasuyukiKita
from the College of Pharmaceutical Sciences at Ritsumeikan University in Shiga,
Japan, and Hiromichi Fujioka from the Graduate School of Pharmaceutical
SciencesatOsakaUniversityinJapancompiledintheirjointchapterthesynthesis
of marine pyrroloiminoquinone alkaloids. The penultimate chapter by Martin G.
Banwell, Nadia Gao, Brett D. Schwarz and Lorenzo V. White from the Research
SchoolofChemistryandInstituteofAdvancedStudiesatTheAustralianNational
UniversityinCanberra,Australia,reportonAmaryllidaceaeandotherterrestrially-
derivedalkaloids.Finally,anarticlewithIngmarBauerasco-authorfromourown
laboratoriesoftheDepartmentofChemistryattheTechnicalUniversityofDresden
ix