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Makrocyclisierung Durch Ringschlussmetathese Bei Der Totalsynthese Von Naturstoffen: Reaktionsbedingungen Und Grenzen

Ana Gradillas, Javier Pérez-Castells
Published 2006 · Chemistry

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Der Aufbau von Makrocyclen durch Ringschlussmetathese (RCM) ist oft eine Schlusselstufe bei der Synthese von Naturstoffen mit grosen Ringen. Diese Reaktion bietet sich an wegen ihrer hohen Toleranz fur funktionelle Gruppen sowie der Moglichkeit zu nachfolgenden Umwandlungen. Dabei ist die Wahl geeigneter Reaktionsbedingungen fur den Erfolg der Synthese entscheidend. Im folgenden Aufsatz fassen wir Arbeiten zusammen, die sich mit der Entwicklung effizienter RCM-Reaktionen im Rahmen der Totalsynthese makrocyclischer Naturstoffe befassen. Dies soll helfen, bei zukunftigen Synthesen die zeitraubende Phase der Optimierung der Reaktionsbedingungen zu reduzieren.
This paper references
10.1021/JA9719945
Total Syntheses of (+)-Ricinelaidic Acid Lactone and of (−)-Gloeosporone Based on Transition-Metal-Catalyzed C−C Bond Formations
A. Fürstner (1997)
10.1055/S-1997-4472
Macrocycles by Ring-Closing Metathesis
A. Fürstner (1997)
10.1021/JO980896E
Remarkable Effect of Ethylene Gas in the Intramolecular Enyne Metathesis of Terminal Alkynes.
M. Mori (1998)
10.1016/S0040-4039(98)01651-7
RU(II)-CATALYZED RCM REACTIONS WITH ELECTROPHILIC DIENE SUBSTRATES
S. Krikštolaitytė (1998)
10.1021/JO971918K
Metathesis Route to Resin Glycosides: Formal Total Synthesis of Tricolorin A.
A. Fürstner (1998)
10.1021/JA974131K
Ruthenium-Catalyzed Olefin Metathesis: A Quantum Molecular Dynamics Study
O. Aagaard (1998)
10.1039/A703881J
Ring closing diene metathesis in organic synthesis
S. Armstrong (1998)
10.1016/S0040-4020(97)10427-6
Recent advances in olefin metathesis and its application in organic synthesis
R. Grubbs (1998)
10.1021/JO981821D
Further Studies on Total Synthesis of Sarain A. Efforts Toward Annulation of the Macrocyclic Rings
O. Irie (1999)
10.1021/JA9829259
ENANTIOSELECTIVE TOTAL SYNTHESES OF IRCINAL A AND RELATED MANZAMINE ALKALOIDS
S. Martin (1999)
10.1021/JA992074K
Ring Closing Alkyne Metathesis. Comparative Investigation of Two Different Catalyst Systems and Application to the Stereoselective Synthesis of Olfactory Lactones, Azamacrolides, and the Macrocyclic Perimeter of the Marine Alkaloid Nakadomarin A
A. Fürstner (1999)
10.1021/OL991029E
Cytotoxic alkaloids motuporamines A-C: synthesis and structural verification.
W. P. Goldring (1999)
10.1021/OL9905912
An enyne metathesis/(4 + 2)-dimerization route to (+/-)-differolide.
T. Hoye (1999)
10.1021/JA983222U
A Recyclable Ru-Based Metathesis Catalyst
Jason S. Kingsbury (1999)
10.1021/OL990947+
Some allylic substituent effects in ring-closing metathesis reactions: allylic alcohol activation.
T. Hoye (1999)
10.1021/JA991361L
Efficient Total Syntheses of Resin Glycosides and Analogues by Ring-Closing Olefin Metathesis
A. Fürstner (1999)
10.1021/OL990909Q
Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands.
M. Scholl (1999)
10.1016/S0040-4020(99)00302-6
Macrocycles by Ring-Closing-Metathesis, XI: Syntheses of (R)-(+)-Lasiodiplodin, Zeranol and Truncated Salicylihalamides
A. Fürstner (1999)
10.1002/1521-3757(20000901)112:17<3140::AID-ANGE3140>3.0.CO;2-G
Olefinmetathese und mehr
Alois Fürstner (2000)
10.1021/CR990407Q
Metal-mediated synthesis of medium-sized rings.
L. Yet (2000)
10.1016/S0040-4039(99)02263-7
Homologation of allylic alcohols. An approach to cyclic and acyclic polyoxygenated compounds
Ryan J Davoille (2000)
10.1021/JA003119G
Novel and Flexible Entries into Prostaglandins and Analogues Based on Ring Closing Alkyne Metathesis or Alkyne Cross Metathesis
A. Fürstner (2000)
10.1021/OL005903B
An imine addition/ring-closing metathesis approach to the spirocyclic core of halichlorine and pinnaic acid.
D. Wright (2000)
10.1016/S0022-328X(00)00096-6
Ring closing alkyne metathesis: stereoselective synthesis of civetone
A. Fürstner (2000)
10.1021/JO991944D
Ring-closing alkyne metathesis. Stereoselective synthesis of the cytotoxic marine alkaloid motuporamine C.
A. Fürstner (2000)
10.1021/JA001179G
Efficient and Recyclable Monomeric and Dendritic Ru-Based Metathesis Catalysts
Steven B. Garber (2000)
10.1002/1521-3757(20000616)112:12<2153::AID-ANGE2153>3.0.CO;2-X
Synthese von mittleren Ringen durch Ringschluss‐Metathese‐Reaktion
M. E. Maier (2000)
10.1021/JO0012952
Ring-closing alkyne metathesis. Application to the total synthesis of sophorolipid lactone.
A. Fürstner (2000)
10.1002/(SICI)1521-3773(20000502)39:9<1664::AID-ANIE1664>3.0.CO;2-#
The Synthesis of Streptogramin Antibiotics: (−)‐Griseoviridin and Its C‐8 Epimer
C. Dvorak (2000)
10.1002/1521-3773(20001201)39:23<4308::AID-ANIE4308>3.0.CO;2-4
Revision of the Absolute Configuration of Salicylihalamide A through Asymmetric Total Synthesis.
Yusheng Wu (2000)
10.1021/OL006059S
Stereoselectivity of macrocyclic ring-closing olefin metathesis
Lee (2000)
10.1002/1521-3773(20000901)39:17<3012::AID-ANIE3012>3.0.CO;2-G
Olefin Metathesis and Beyond
A. Fürstner (2000)
10.1002/1521-3773(20000616)39:12<2073::AID-ANIE2073>3.0.CO;2-0
Synthesis of Medium-Sized Rings by the Ring-Closing Metathesis Reaction.
Maier (2000)
10.1021/JA011242H
Synthesis and absolute stereochemistry of roseophilin.
P. Harrington (2001)
10.1021/JA011271S
Asymmetric total synthesis of ent-(-)-roseophilin: assignment of absolute configuration.
D. Boger (2001)
10.1021/OM010314A
Novel η^3- Vinylcarbene Complexes Derived from Ruthenium-Based Olefin Metathesis Catalysts
T. M. Trnka (2001)
10.1021/JO0158480
Formation of macrocycles via ring-closing olefin metathesis.
C. W. Lee (2001)
10.1016/S0040-4039(01)00449-X
Temperature-dependent isomerisation versus net fragmentation of secondary allylic alcohols with Grubbs’ catalyst
M. K. Gurjar (2001)
10.1021/JA010313+
Teubrevin G and teubrevin H: the first total syntheses of rearranged neo-clerodanes including solutions to the problems of chirality merger and furan ring assembly.
L. Paquette (2001)
10.1021/JA0106164
Total synthesis of (-)-cylindrocyclophanes A and F exploiting the reversible nature of the olefin cross metathesis reaction.
A. Smith (2001)
10.1039/B101453F
Unexpected results of enyne metathesis using a ruthenium complex containing an N-heterocyclic carbene ligand
T. Kitamura (2001)
10.1021/JA003582T
New insights into the mechanism of ruthenium-catalyzed olefin metathesis reactions.
M. Sanford (2001)
10.1021/AR000114F
The development of L2X2Ru=CHR olefin metathesis catalysts: an organometallic success story.
T. Trnka (2001)
10.1002/1521-3765(20010803)7:15<3236::AID-CHEM3236>3.0.CO;2-S
Comparative investigation of ruthenium-based metathesis catalysts bearing N-heterocyclic carbene (NHC) ligands.
A. Fürstner (2001)
10.1002/1521-3765(20011217)7:24<5286::AID-CHEM5286>3.0.CO;2-G
Total synthesis of (-)-salicylihalamide.
A. Fürstner (2001)
10.1021/JA011364+
Concise asymmetric syntheses of radicicol and monocillin I.
R. Garbaccio (2001)
10.1021/JA010624K
Mechanism and activity of ruthenium olefin metathesis catalysts.
M. Sanford (2001)
10.1021/JA016431E
Tandem catalysis: the sequential mediation of olefin metathesis, hydrogenation, and hydrogen transfer with single-component Ru complexes.
J. Louie (2001)
10.1021/OL017298Y
Synthesis of cyclic dienamide using ruthenium-catalyzed ring-closing metathesis of ene-ynamide.
N. Saito (2002)
10.1002/ANIE.200290042
Total synthesis of amphidinolide T4.
A. Fürstner (2002)
10.1021/OL0262284
Total synthesis of proposed amphidinolide A via a highly selective ring-closing metathesis.
R. Maleczka (2002)
10.1002/1521-3765(20020415)8:8<1856::AID-CHEM1856>3.0.CO;2-R
Total synthesis of the turrianes and evaluation of the DNA-cleaving properties.
A. Fürstner (2002)
10.1021/JA020259C
A recyclable chiral Ru catalyst for enantioselective olefin metathesis. Efficient catalytic asymmetric ring-opening/cross metathesis in air.
J. V. Van Veldhuizen (2002)
10.1016/S0040-4039(02)00111-9
Effect of a proximal oxygen substituent on the efficacy of ruthenium-catalyzed cross-metathesis and RCM
T. Maishal (2002)
10.1002/1521-3773(20020301)41:5<794::AID-ANIE794>3.0.CO;2-B
A highly active and air-stable ruthenium complex for olefin metathesis.
Hideaki Wakamatsu (2002)
10.1021/JA027883+
Ruthenium-catalyzed alkene-alkyne coupling: synthesis of the proposed structure of amphidinolide A.
B. Trost (2002)
10.1002/1521-3765(20020902)8:17<3962::AID-CHEM3962>3.0.CO;2-X
Mechanism of olefin metathesis with catalysis by ruthenium carbene complexes: density functional studies on model systems.
S. Vyboishchikov (2002)
10.1002/1521-3773(20020201)41:3<508::AID-ANIE508>3.0.CO;2-7
Total synthesis of the presumed amphidinolide A.
H. W. Lam (2002)
10.1021/JO0200062
Carbohydrate carbocyclization by a zinc-mediated tandem reaction and ring-closing enyne metathesis.
C. S. Poulsen (2002)
10.1002/ANGE.200290041
Totalsynthese von Amphidinolid T4
A. Fürstner (2002)
10.1021/JA0202964
Enantioselective total syntheses of manzamine a and related alkaloids.
J. Humphrey (2002)
10.1002/1521-3773(20020617)41:12<2097::AID-ANIE2097>3.0.CO;2-T
Total synthesis of woodrosin I.
A. Fürstner (2002)
10.1021/JA016585U
Biomimetic synthesis of (-)-longithorone A.
M. E. Layton (2002)
10.1002/ANIE.200390103
A catalytic approach to (R)-(+)-muscopyridine with integrated "self-clearance".
A. Fürstner (2003)
10.1021/JO026686Q
Total synthesis of (s)-(+)-citreofuran by ring closing alkyne metathesis.
A. Fürstner (2003)
10.1021/OL0350689
New strategy for the total synthesis of macrosphelides a and B based on ring-closing metathesis.
Y. Matsuya (2003)
10.1021/OL035014Z
Conjugated enynes as a new type of substrates for olefin metathesis.
B. Kang (2003)
10.1021/CR030035S
Chemistry and biology of salicylihalamide a and related compounds.
L. Yet (2003)
10.1021/JA0349103
The total synthesis of (+)-migrastatin.
C. Gaul (2003)
10.1002/CHEM.200390026
Total synthesis of woodrosin I--part 2: final stages involving RCM and an orthoester rearrangement.
A. Fürstner (2003)
10.1021/OL035309C
Total synthesis and conformational analysis of the antifungal agent (-)-PF1163B.
Fodil Bouazza (2003)
10.1002/ANIE.200352413
Catalysis-based total synthesis of latrunculin B.
A. Fürstner (2003)
10.1021/JA021146W
Synthesis and activity of ruthenium alkylidene complexes coordinated with phosphine and N-heterocyclic carbene ligands.
T. M. Trnka (2003)
10.1016/S0040-4020(03)01029-9
Ruthenium olefin metathesis catalysts with modified styrene ethers: influence of steric and electronic effects
M. Zaja (2003)
10.1021/JA034464J
The first total synthesis of nakadomarin A.
Toshiaki Nagata (2003)
10.1021/JO026914G
Synthetic studies toward sarain A. Formation of the western macrocyclic ring.
M. Sung (2003)
10.1016/S0040-4039(03)00618-X
Effects of temperature and concentration in some ring closing metathesis reactions
K. Yamamoto (2003)
10.1016/S0040-4039(03)00346-0
A highly efficient olefin metathesis initiator: improved synthesis and reactivity studies
Aideen M. Dunne (2003)
10.1002/ANGE.200390071
Ein katalytischer Zugang zu (R)‐(+)‐Muscopyridin mit integrierter Selbstreinigung
A. Fürstner (2003)
10.1002/ANGE.200301628
Neue Methoden zur Bildung von (E)‐Alken‐Einheiten in makrocyclischen Naturstoffen
Joëlle Prunet (2003)
10.1002/EJOC.200300102
Synthesis of Carbohydrate-Derived Enynes and Subsequent Metathesis to Yield Polyhydroxylated 1-Vinylcycloalkenes
Franck Dolhem (2003)
10.1002/ANIE.200301628
Recent methods for the synthesis of (E)-alkene units in macrocyclic natural products.
J. Prunet (2003)
10.1021/JA035579Q
Macrolactonization via Ti(IV)-mediated epoxy-acid coupling: a total synthesis of (-)-dactylolide [and zampanolide].
T. Hoye (2003)
10.1021/JA038216Z
Total syntheses of amphidinolide T1, T3, T4, and T5.
C. Aïssa (2003)
10.1021/JA0488380
Decomposition of a key intermediate in ruthenium-catalyzed olefin metathesis reactions.
S. H. Hong (2004)
10.1002/ANIE.200453663
Total synthesis and structural assignment of spongidepsin through a stereodivergent ring-closing-metathesis strategy.
Jiehao Chen (2004)
10.1021/JA048794V
Nitro-substituted Hoveyda-Grubbs ruthenium carbenes: enhancement of catalyst activity through electronic activation.
A. Michrowska (2004)
10.1002/ANIE.200454108
Modular asymmetric synthesis of pochonin C.
S. Barluenga (2004)
10.1021/OL0400037
First total synthesis of trans- and cis-resorcylide: remarkable hydrogen-bond-controlled, stereospecific ring-closing metathesis.
E. Couladouros (2004)
10.1021/JO049222W
Ortho- and para-substituted Hoveyda-Grubbs carbenes. An improved synthesis of highly efficient metathesis initiators.
R. Bujok (2004)
10.1021/OL036284K
A convergent synthesis of the macrocyclic core of cytotrienins: application of RCM for macrocyclization.
G. Evano (2004)
10.1002/ANIE.200461802
A formal total synthesis of (+)-pinnatoxin A.
S. Sakamoto (2004)
10.1021/OL036062M
Tandem RCM of dienynes for the construction of taxol-type carbocyclic systems.
Rebeca García-Fandiño (2004)
10.1002/ANIE.200460042
Total synthesis of the salicylate enamide macrolide oximidine III: application of relay ring-closing metathesis.
Xiang Wang (2004)
10.1002/CHEM.200400617
Total synthesis of salicylihalamides A and B.
C. Herb (2004)
10.1021/OL036258M
Total synthesis of aigialomycin D.
X. Geng (2004)
10.1073/PNAS.0401322101
Catalysis-based enantioselective total synthesis of the macrocyclic spermidine alkaloid isooncinotine.
B. Scheiper (2004)
10.1039/B311496C
Ru complexes bearing bidentate carbenes: from innocent curiosity to uniquely effective catalysts for olefin metathesis.
A. Hoveyda (2004)
10.1021/CR0200872
Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis.
A. Deiters (2004)
10.1021/CR020009E
Enyne metathesis (enyne bond reorganization).
S. Diver (2004)
10.1016/J.TETLET.2004.04.164
RCM approach for the total synthesis of cryptophycin-24 (Arenastatin A)
N. K. Tripathy (2004)
10.1021/JA0484348
New efficient synthesis of resorcinylic macrolides via ynolides: establishment of cycloproparadicicol as synthetically feasible preclinical anticancer agent based on Hsp90 as the target.
Zhi-qiang Yang (2004)
10.1002/EJOC.200300714
Catalysis at the Interface of Ruthenium Carbene and Ruthenium Hydride Chemistry: Organometallic Aspects and Applications to Organic Synthesis
B. Schmidt (2004)
10.1002/ANGE.200500369
Metathesereaktionen in der Totalsynthese
K. Nicolaou (2005)
10.1002/ANIE.200500390
Concise and practical synthesis of latrunculin a by ring-closing enyne-yne metathesis.
A. Fürstner (2005)
10.1021/OL047559E
Total synthesis and elucidation of the absolute configuration of the diterpene tonantzitlolone.
C. Jasper (2005)
10.1039/B512877C
Total synthesis of aspercyclide C.
A. Fürstner (2005)
10.1021/JA0509984
The total synthesis of coleophomones B, C, and D.
K. Nicolaou (2005)
10.1002/ANIE.200500369
Metathesis reactions in total synthesis.
K. Nicolaou (2005)
10.1002/9783527619481.CH17
Ene‐Yne Metathesis
M. Mori (2008)



This paper is referenced by
10.1002/SLCT.202004765
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J. J. Jun (2021)
10.1002/asia.202001015
Unified Total Synthesis of (-)-Enigmazole A and (-)-15-O-Methylenigmazole A.
K. Sakurai (2020)
10.1002/ejoc.202000513
A Concise Synthesis of the Key Tetrahydrofuran Moieties of Caruifolin A and EBC‐342
R. A. Fernandes (2020)
10.1002/ajoc.202000294
Synthesis of C9‐C13 and C15‐C21 Subunits of Discodermolide
Debjani Si (2020)
10.1002/chem.201900813
Total Synthesis, Stereochemical Revision, and Biological Assessment of Iriomoteolide-2a.
Keita Sakamoto (2019)
10.1002/adsc.201901132
Phosphine‐Catalyzed Chemoselective [4+3] Cycloaddition of Alminine Esters and β′‐acetoxy Allenoates for Divergent Synthesis of Azepines
Zonghao Dai (2020)
10.1002/EJOC.201801307
Hindered Urea Bond: A Bilaterally Responsive Chemistry to Hydrogen Peroxide
Hanze Ying (2019)
10.1002/SLCT.201801117
Natural Product Inspired Topology Directed Synthesis of Hybrid Macrocyclic Compounds: A Simple Approach to Natural Product Analogues
N. R. Gade (2018)
10.1002/chem.201800728
Sequential Alkene Isomerization and Ring-Closing Metathesis in Production of Macrocyclic Musks from Biomass.
Adrian Sytniczuk (2018)
10.1002/anie.201809076
Total Synthesis of an Atropisomer of the Schisandra Triterpenoid Schiglautone A.
B. Ma (2018)
10.1002/ANGE.201802563
Eisenkatalysierte C‐O/C‐O‐Bindungsmetathese von aliphatischen Ethern
Tobias Biberger (2018)
10.1002/ange.201809076
Total Synthesis of an Atropisomer of the Schisandra Triterpenoid Schiglautone A
Binjie Ma (2018)
10.1002/chem.201504832
One-Pot Approach to Organo-Phosphorus-Chalcogen Macrocycles Incorporating Double OP(S)SCn or OP(Se)SeCn Scaffolds: A Synthetic and Structural Study.
Guoxiong Hua (2016)
10.1002/chem.201600341
Total Synthesis and Complete Stereostructure of a Marine Macrolide Glycoside, (-)-Lyngbyaloside B.
H. Fuwa (2016)
10.1002/chem.201501983
Macrocyclic weakly coordinating anions.
Kai Landskron (2015)
10.1002/chem.201501423
Evolution of a Unified Strategy for Complex Sesterterpenoids: Progress toward Astellatol and the Total Synthesis of (-)-Nitidasin.
Daniel T. Hog (2015)
10.1002/chem.201502132
Total Synthesis and Structural Reassignment of Lyngbyaloside C Highlighted by Intermolecular Ketene Esterification.
Chia-Fu Chang (2015)
10.1002/chem.201403176
Synthesis and evaluation of novel analogues of ripostatins.
Wufeng Tang (2014)
10.1002/EJOC.201301493
Diversity‐Oriented Approach to Normuscopyridine and Its Analogues through Ring‐Closing Metathesis
S. Kotha (2014)
10.1002/chem.201403704
Cyclooctane metathesis catalyzed by silica-supported tungsten pentamethyl [(≡SiO)W(Me)5]: distribution of macrocyclic alkanes.
N. Riache (2014)
10.1002/anie.201406486
Gold-catalyzed 1,2-acyloxy migration/intramolecular [3+2] 1,3-dipolar cycloaddtion cascade reaction: an efficient strategy for syntheses of medium-sized-ring ethers and amines.
C. Zhao (2014)
10.1002/EJOC.201300083
Towards the Synthesis of Lyngbyaloside B: Stereoselective Synthesis of the C1–C16 Macrolactone Core Segment
J. S. Yadav (2013)
10.1002/ANGE.201303916
Übergangsmetallkatalysierte C‐C‐Kupplungen mit Ethylen im Labormaßstab
Vaneet Saini (2013)
10.1002/EJIC.201200966
Synthesis and Characterization of Sterically Enlarged Hoveyda‐Type Olefin Metathesis Catalysts
S. Shahane (2013)
10.1002/chem.201201843
Macrocyclic architecture: tuning cavity size and shape through maleimide photochemistry.
Kara L. Cubbage (2012)
10.1002/asia.201100780
Chemical synthesis of the englerins.
Rebecca H. Pouwer (2012)
10.1002/EJOC.201001562
Chemical Synthesis and Biological Evaluation of Second-Generation Palmerolide A Analogues
V. Ravu (2011)
10.1002/chem.201003135
Total synthesis and biological assessment of (-)-exiguolide and analogues.
H. Fuwa (2011)
10.1002/chem.201100483
The pivotal role of symmetry in the ruthenium-catalyzed ring-closing metathesis of olefins.
C. Costabile (2011)
10.1039/c1ob05787a
A flexible and unified strategy for syntheses of cladospolides A, B, C, and iso-cladospolide B.
Debjani Si (2011)
10.1002/asia.201000534
Rapid assembly of resorcylic acid lactone frameworks through sequential palladium-catalyzed coupling reactions.
Shinichiro Fuse (2010)
10.1002/anie.201000624
A concise total synthesis of (+)-neopeltolide.
H. Fuwa (2010)
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