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Metathesis Reactions In Total Synthesis.

K. Nicolaou, P. Bulger, D. Sarlah
Published 2005 · Chemistry, Medicine

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With the exception of palladium-catalyzed cross-couplings, no other group of reactions has had such a profound impact on the formation of carbon-carbon bonds and the art of total synthesis in the last quarter of a century than the metathesis reactions of olefins, enynes, and alkynes. Herein, we highlight a number of selected examples of total syntheses in which such processes played a crucial role and which imparted to these endeavors certain elements of novelty, elegance, and efficiency. Judging from their short but impressive history, the influence of these reactions in chemical synthesis is destined to increase.
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Alkinmetathese als neues Synthesewerkzeug: ringschließend, ringöffnend und acyclisch
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Design of Bifunctional Antibiotics that Target Bacterial rRNA and Inhibit Resistance-Causing Enzymes
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Dimeric malarial drugs for enhanced activity.
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New Approaches to Olefin Cross-Metathesis
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Enantioselective Synthesis of Tetraponerines by Pd- and Ru-Catalyzed Domino Reactions
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A new and efficient synthetic route to enantiopure (+)-anatoxin-a from (−)-cocaine hydrochloride
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Simple Total Synthesis of the Pentacyclic Cs-Symmetric Structure Attributed to the Squalenoid Glabrescol and Three Cs-Symmetric Diastereomers Compel Structural Revision
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Sequential Intramolecular Cyclobutadiene Cycloaddition, Ring-Opening Metathesis, and Cope Rearrangement: Total Syntheses of (+)- and (−)-Asteriscanolide
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An Asymmetric Synthesis of the Tricyclic Core and a Formal Total Synthesis of Roseophilin via an Enyne Metathesis
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Olefinmetathese und mehr
Alois Fürstner (2000)
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Bimetallic catalytic cascade ring closing metathesis—intramolecular Heck reactions using a fluorous biphasic solvent system or a polymer-supported palladium catalyst
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What Is the Structure of Glabrescol? Stereoselective Synthesis of Reported Glabrescol
Hideaki Hioki (2000)
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A modular synthetic approach toward exhaustively stereodiversified ligand libraries.
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Concise synthesis of (S,S)-(+)-dehydrohomoancepsenolide.
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Revised Structure of Squalene-Derived PentaTHF Polyether, Glabrescol, through Its Enantioselective Total Synthesis: Biogenetically Intriguing Cs vs C2 Symmetric Relationships
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Improvement in olefin metathesis using a new generation of ruthenium catalyst bearing an imidazolylidene ligand: synthesis of heterocycles
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Total synthesis of everninomicin 13,384-1--Part 3: synthesis of the DE fragment and completion of the total synthesis.
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Simple Enantioselective Total Synthesis of Glabrescol, a Chiral C2-Symmetric Pentacyclic Oxasqualenoid
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Synthesis of the First "Inside-Outside" Eight-Membered Ring via Ring-Closing Metathesis: A Total Synthesis of (±)-Asteriscanolide
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Efficient and Recyclable Monomeric and Dendritic Ru-Based Metathesis Catalysts
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Terminal Alkyne-Ethylene Cross-Metathesis: Reaction of 1-Substituted Propargyl Esters at Elevated Ethylene Pressure.
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Synthese von mittleren Ringen durch Ringschluss‐Metathese‐Reaktion
M. E. Maier (2000)
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Ring-closing alkyne metathesis. Application to the total synthesis of sophorolipid lactone.
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The Synthesis of Streptogramin Antibiotics: (−)‐Griseoviridin and Its C‐8 Epimer
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Total synthesis of everninomicin 13,384-1--Part 2: synthesis of the FGHA2 fragment.
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Ring Closing Metathesis Directed Synthesis of (R)-(−)-Muscone from (+)-Citronellal
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Facile Synthesis of Trialkoxymolybdenum(VI) Alkylidyne Complexes for Alkyne Metathesis
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Total Syntheses of (±)- and (−)-Stemoamide
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Biomimetic synthesis of alkaloids.
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Synthesis and metathesis reactions of a phosphine-free dihydroimidazole carbene ruthenium complex
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Diastereoselective ring-closing metathesis in the synthesis of dihydropyrans
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Olefin Metathesis and Beyond
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Stereoselective double ring closing metathesis reactions in the synthesis of spirocyclic compounds
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Recent applications of olefin metathesis and relatedreactions in carbohydrate chemistry
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Total synthesis of everninomicin 13,384-1--Part 1: retrosynthetic analysis and synthesis of the A1B(A)C fragment.
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A related metathesis-based approach to the ingenol ABC-ring core structure
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A double ring closing metathesis reaction in the rapid, enantioselective synthesis of NK-1 receptor antagonists.
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Progress toward the total synthesis of ingenol: construction of the complete carbocyclic skeleton.
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Recent developments in the chemistry, biology and medicine of the epothilones.
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Stereocontrolled syntheses of epimeric 3-aryl-6-phenyl-1-oxa-7-azaspiro(4.5)decane NK-1 receptor antagonist precursors.
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Triple ring closing metathesis reaction: synthesis of adjacent cyclic ethers.
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Catalytic asymmetric olefin metathesis.
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Total Synthesis of Ciguatoxin CTX3C
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Alkyne metathesis: development of a novel molybdenum-based catalyst system and its application to the total synthesis of epothilone A and C.
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The stereochemistry of glabrescol
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Ingenol esters induce apoptosis in Jurkat cells through an AP-1 and NF-kappaB independent pathway.
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Total synthesis of (-)-cylindrocyclophanes A and F exploiting the reversible nature of the olefin cross metathesis reaction.
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Tandem dienyne cross-metathesis/ring-closing metathesis
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Total synthesis of (+/-)-asteriscanolide.
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C-glycosides to fused polycyclic ethers. An efficient entry into the A-D ring system of gambierol.
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The first general method for palladium-catalyzed Negishi cross-coupling of aryl and vinyl chlorides: use of commercially available Pd(P(t-Bu)(3))(2) as a catalyst.
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The development of L2X2Ru=CHR olefin metathesis catalysts: an organometallic success story.
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Comparative investigation of ruthenium-based metathesis catalysts bearing N-heterocyclic carbene (NHC) ligands.
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Iridium(I)-catalyzed cycloisomerization of enynes.
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Total synthesis of (-)-salicylihalamide.
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Concise asymmetric syntheses of radicicol and monocillin I.
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An enyne metathesis approach to the synthesis of the 1,3-diene system of mycothiazole
Sara Rodrı́guez-Conesa (2001)
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Synthesis and biological evaluation of vancomycin dimers with potent activity against vancomycin-resistant bacteria: target-accelerated combinatorial synthesis.
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The synthesis of an exhaustively stereodiversified library of cis-1,5 enediols by silyl-tethered ring-closing metathesis.
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Synthesis of (-)-deoxypukalide, the enantiomer of a degradation product of the furanocembranolide pukalide.
James A. Marshall and (2001)
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Siloxyalkyne-Alkene Metathesis: Rapid Access to Highly Functionalized Enones.
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Solid- and solution-phase synthesis of vancomycin and vancomycin analogues with activity against vancomycin-resistant bacteria.
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Tandem catalysis: the sequential mediation of olefin metathesis, hydrogenation, and hydrogen transfer with single-component Ru complexes.
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Identification and Isolation of a Receptor for N-Methyl Alkylammonium Salts: Molecular Amplification in a Pseudo-peptide Dynamic Combinatorial Library.
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Dynamic Combinatorial Chemistry
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Concise total syntheses of epothilone A and C based on alkyne metathesis
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Sequential ring-closing metathesis and silicon-assisted cross-coupling reactions: stereocontrolled synthesis of highly substituted unsaturated alcohols.
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Enantioselective ruthenium-catalyzed ring-closing metathesis.
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For a discussion of this phenomenon as applied to related systems , see : J . A . Marshall , E . V . Van Devender
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For studies towards the synthesis of the marine sponge metabolite mycothiazole A in which an enyne cross-metathesis reaction was employed to fashion a key 1,3-diene
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A chemo- and stereoselective reduction of cycloalkynes to (E)-cycloalkenes.
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Application of hitherto unexplored macrocyclization strategies in the epothilone series: novel epothilone analogs by total synthesis.
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Discovery of exceptionally efficient catalysts for solvent-free enantioselective hetero-Diels-Alder reaction.
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The first total synthesis of (+/-)-ingenol.
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An improved catalyst for ring-closing alkyne metathesis based on molybdenum hexacarbonyl/2-fluorophenol.
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Synthetic studies on the ingenane diterpenes. An improved entry into a trans-intrabridgehead system.
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Unexpected Dramatic Substituent Effect for Tuning the Selectivity in the Double Ring-Closing Metathesis Reaction of N-Containing Tetraenes. An Efficient Synthesis of Bicyclic Izidine Alkaloid Skeletons
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Total syntheses of the phytotoxic lactones herbarumin I and II and a synthesis-based solution of the pinolidoxin puzzle.
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Studies on the biomimetic synthesis of SNF4435 C and D.
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Total synthesis of amphidinolide T4.
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The Diels--Alder reaction in total synthesis.
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Facile synthesis of a selectively protected triazamacrocycle
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Self-terminating, oxidative radical cyclizations: a novel reaction of acyloxyl radicals.
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Total synthesis of proposed amphidinolide A via a highly selective ring-closing metathesis.
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Total synthesis of the turrianes and evaluation of the DNA-cleaving properties.
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An improved 1,3-diene synthesis from alkyne and ethylene using cross-enyne metathesis
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A recyclable chiral Ru catalyst for enantioselective olefin metathesis. Efficient catalytic asymmetric ring-opening/cross metathesis in air.
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Ein selbstgenerierender, hochaktiver und wiederverwendbarer Katalysator für die Olefinmetathese†
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The total synthesis of coleophomones B and C.
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A stereoselective route to guanacastepene A through a surprising epoxidation.
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Systematic Analysis of the Intramolecular Competition Associated with the Ring Closing Metathesis of Ene-Diene Systems of Differing Chain Length with a Pair of Ruthenium Catalysts
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A self-generating, highly active, and recyclable olefin-metathesis catalyst.
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Skeletal reorganization of enynes to 1-vinylcycloalkenes catalyzed by GaCl(3).
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N-Heterocyclische Carbene: ein neues Konzept in der metallorganischen Katalyse
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A new highly efficient ruthenium metathesis catalyst.
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N-heterocyclic carbenes: a new concept in organometallic catalysis.
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[4 + 1] cycloaddition of N-heterocyclic carbenes with vinyl isocyanates.
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Carbohydrate based formal synthesis of stemoamide using ring-closing metathesis
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Stereoselective total synthesis of mucocin, an antitumor agent.
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Total synthesis of the presumed amphidinolide A.
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Metathesis of Electron-Rich Olefins: Structure and Reactivity of Electron-Rich Carbene Complexes
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Highly concise routes to epothilones: the total synthesis and evaluation of epothilone 490.
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Synthesis of the functionalized tricyclic skeleton of guanacastepene A: a tandem epoxide-opening beta-elimination/knoevenagel cyclization.
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Catalytic asymmetric intramolecular aminopalladation: enantioselective synthesis of vinyl-substituted 2-oxazolidinones, 2-imidazolidinones, and 2-pyrrolidinones.
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Totalsynthese von Amphidinolid T4
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Silicon tether-aided coupling metathesis: application to the synthesis of attenol A.
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Total synthesis of woodrosin I.
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Practical total synthesis of ciguatoxin CTX3C by improved protective group strategy.
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Total synthesis of (+)-dihydrocuscohygrine and cuscohygrine.
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Die Diels‐Alder‐Reaktion in der Totalsynthese
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Biomimetic synthesis of (-)-longithorone A.
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Total synthesis of an antitumor agent, mucocin, based on the "chiron approach".
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Virus-ligand interactions: identification and characterization of ligand binding by NMR spectroscopy.
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A concise route to benzofused macrolactones via ynolides: cycloproparadicicol.
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A general model for selectivity in olefin cross metathesis.
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A catalytic approach to (R)-(+)-muscopyridine with integrated "self-clearance".
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Biomimetic total synthesis of litseaverticillols A, C, D, F, and G: singlet-oxygen-initiated cascades.
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Total synthesis of (s)-(+)-citreofuran by ring closing alkyne metathesis.
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Chemie und Biologie des Roseophilins und der Prodigiosin‐Alkaloide: 2500 Jahre im Überblick
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Total synthesis of the proposed azaspiracid-1 structure, part 2: coupling of the C1-C20, C21-C27, and C28-C40 fragments and completion of the synthesis.
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Novel synthesis of heterocycles having a functionalized carbon center via nickel-mediated carboxylation: total synthesis of erythrocarine.
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A route to the thapsigargins from (S)-carvone providing a substrate-controlled total synthesis of trilobolide, nortrilobolide, and thapsivillosin F.
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A stereoselective enyne cross metathesis.
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Synthesis of an F-H gambierol subunit using a C-glycoside-centered strategy.
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Total synthesis of woodrosin I--part 2: final stages involving RCM and an orthoester rearrangement.
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A quadruple ring-closing metathesis reaction in the synthesis of bis-spirocyclic compounds: extending the scope of metathesis chemistry
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Synthesis of functionalized vinyl boronates via ruthenium-catalyzed olefin cross-metathesis and subsequent conversion to vinyl halides.
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