The Olefin Metathesis Approach to Epothilone A and Its Analogues

No abstract is available for this paper.

• Publication year

  1997

• Venue

  Journal of the American Chemical Society

• Publication date

  1997-08-27

• Fields of study

  Chemistry

• Identifiers
  DOI 10.1021/JA971109I
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

• No references are available for this paper.

• Synthesis of Dibenzo‐Fused 15‐Membered Dioxa‐ketone Macrocycles through Ring‐Closing Metathesis Reaction

  2022cites this paper
• E vs Z Selectivity in Olefin Metathesis Through Catalyst Design

  2021cites this paper
• Epothilones A and B: The 16-Membered Natural Macrolides as a Fascinating Template for Antibreast Cancer Drug Discovery

  2021cites this paper
• On the Importance of the Thiazole Nitrogen in Epothilones: Semisynthesis and Microtubule-Binding Affinity of Deaza-Epothilone C

  2020cites this paper
• Perspectives from nearly five decades of total synthesis of natural products and their analogues for biology and medicine.

  2020cites this paper
• Domino Ring Expansion: Regioselective Access to 9-Membered Lactones with a Fused Indole Unit from 2-Nitrophenyl-1,3-cyclohexanediones.

  2018cites this paper
• Recent advances in microtubule-stabilizing agents.

  2018cites this paper
• Ring-Closing Metathesis in Pharmaceutical Development: Fundamentals, Applications, and Future Directions

  2018cites this paper
• Pd-Boron-Catalyzed One Carbon Isomerization of Olefins: Water Assisted Process at Room Temperature.

  2017cites this paper
• The Evolution and Impact of Total Synthesis on Chemistry, Biology and Medicine

  2017cites this paper
• The Total Synthesis of Epothilone D as a Yardstick for Probing New Methodologies.

  2017cites this paper
• Synthesis of Indole Annulated [1,3]‐Thiazaheterocycles and ‐macrocycles via Ring‐Closing Metathesis

  2016cites this paper
• Stereoselective total synthesis of cryptomoscatone D1 and (5R,7S)-kurzilactone via ring closing metathesis

  2016cites this paper
• Synthesis of Macrocycles Other than Peptides by Metathesis

  2015cites this paper
• Enolates with Chiral Auxiliaries in Asymmetric Syntheses

  2015cites this paper
• Application of catalytic Z-selective olefin metathesis in natural product synthesis

  2015cites this paper
• Synthesis and Biological Evaluation of Novel Epothilone B Side Chain Analogues

  2015cites this paper
• 5.29 Ring-Closing Metathesis

  2014cites this paper
• Diversity-oriented approach to spirocycles via ring-closing metathesis

  2014cites this paper
• Applications in the Synthesis of Natural and Biologically Active Molecules

  2014cites this paper
• Evolution of Catalytic Stereoselective Olefin Metathesis: From Ancillary Transformation to Purveyor of Stereochemical Identity

  2014cites this paper
• Small molecule modulators of protein-protein interactions: selected case studies.

  2014cites this paper
• Chemistry and Biology of Epothilones

  2014cites this paper
• Asymmetric α‐Alkylation of Aldehydes, Ketones, and Carboxylic Acids

  2013cites this paper
• Molybdenum-based complexes with two aryloxides and a pentafluoroimido ligand: catalysts for efficient Z-selective synthesis of a macrocyclic trisubstituted alkene by ring-closing metathesis.

  2013cites this paper
• Efficient and selective formation of macrocyclic disubstituted Z alkenes by ring-closing metathesis (RCM) reactions catalyzed by Mo- or W-based monoaryloxide pyrrolide (MAP) complexes: applications to total syntheses of epilachnene, yuzu lactone, ambrettolide, epothilone C, and nakadomarin A.

  2013cites this paper
• An approach to highly oxygenated monocyclic derivatives with large rings

  2013cites this paper
• Epothilone D and its 9-Methyl analogues: combinatorial syntheses, conformation, and biological activities.

  2013cites this paper
• Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

  2012cites this paper
• Design and synthesis of self-degradable antibacterial polymers by simultaneous chain- and step-growth radical copolymerization.

  2012cites this paper
• Synthesis of Triazole‐Epothilones by Using Cu2O Nanoparticles to Catalyze 1,3‐Dipolar Cycloaddition

  2012cites this paper
• C6-C8 bridged epothilones: consequences of installing a conformational lock at the edge of the macrocycle.

  2011cites this paper
• Ruthenium, [1,3‐Bis(2,4,6‐trimethylphenyl)‐2‐imidazolidinylidene]dichloro(phenylmethylene)(tricyclohexylphosphine) (Grubbs' Second‐Generation Catalyst)

  2010cites this paper
• In situ generated bulky palladium hydride complexes as catalysts for the efficient isomerization of olefins. Selective transformation of terminal alkenes to 2-alkenes.

  2010cites this paper
• Synthesis of Natural Products Containing Macrocycles by Alkene Ring‐Closing Metathesis

  2010cites this paper
• An entry to 1,6-dioxaspiro[4.6]undecanes and 1,7-dioxaspiro[5.6]dodecanes

  2010cites this paper
• Ring‐Closing Alkyne Metathesis in Natural Product Synthesis

  2010cites this paper
• Saturated and unsaturated lactones

  2010cites this paper
• From nature to the laboratory and into the clinic.

  2009cites this paper
• Macrolide-based microtubule-stabilizing agents - chemistry and structure-activity relationships.

  2009cites this paper
• Medicinal chemistry of paclitaxel and its analogues.

  2009cites this paper
• Total synthesis of epothilones A-F.

  2009cites this paper
• Total synthesis of diverse carbogenic complexity within the resveratrol class from a common building block.

  2009cites this paper
• Epothilones – A fascinating family of microtubule stabilizing antitumor agents

  2008cites this paper
• 4.06 – Thiazoles

  2008cites this paper
• The Chemistry and Biology of Epothilones—The Wheel Keeps Turning

  2007cites this paper
• Organische Totalsynthese – Quo vadis?

  2007cites this paper
• Alkyne Metathesis: Catalysts and Synthetic Applications

  2007cites this paper
• An improved procedure for the separation of (+) or (-)-isopinocampheol, the major side product of the oxidation workup procedure of Brown's asymmetric crotylborations

  2007cites this paper
• [2,6‐Bis(1‐methylethyl)benzenaminato‐(2) [bis(1,1,1,3,3,3‐hexafluoro‐2‐methyl‐2‐ propanolato)(2‐methyl‐2‐phenylpropylidene) molybdenum (Schrock's Catalyst)

  2006cites this paper
• Organic Synthesis Using Metal‐Mediated Metathesis Reactions

  2006cites this paper
• Modern aldol methods for the total synthesis of polyketides.

  2006cites this paper
• Aldolreaktionen in der Totalsynthese von Polyketiden

  2006cites this paper
• Epothilone, a Myxobacterial Metabolite with Promising Antitumor Activity

  2005cites this paper
• Metathesis reactions in total synthesis.

  2005cites this paper
• Singular Features of Hydrolysis of Partially Blocked β,δ-Dihydroxy Enol Ether from Pantolactone

  2005cites this paper
• Total synthesis of 12,13-desoxyepothilone B (Epothilone D).

  2005cites this paper
• Metathesereaktionen in der Totalsynthese

  2005cites this paper
• Studies towards the synthesis of epothilone A via organoboranes.

  2005cites this paper
• Asymmetric aldol reactions using catalytic d(+)-proline: a new, economic and practical approach to a commonly employed C1–C6 keto-acid synthon of the epothilones

  2004cites this paper
• The merger of natural product synthesis and medicinal chemistry: on the chemistry and chemical biology of epothilones.

  2004cites this paper
• 4. The natural products epothilones A and B as lead structures for anticancer drug discovery: chemistry, biology, and SAR studies.

  2004cites this paper
• Synthesis and Conformational Analysis of Macrocycles Related to 10-Oxa-epothilone

  2004cites this paper
• Dioxirane Epoxidation of Alkenes

  2004cites this paper
• Access to ring-fused azepino[3,4-b]indole-1,5-dione derivatives by ring-closing olefin metathesis

  2004cites this paper
• Synthetic studies towards the phomactins. Concise syntheses of the tricyclic furanochroman and the oxygenated bicyclo[9.3.1]pentadecane ring systems in phomactin A.

  2003cites this paper
• N-Bromosuccinimide-dibenzoyl peroxide/azabisisobutyronitrile: a reagent for Z- to E-alkene isomerization

  2003cites this paper
• Total Synthesis of Macrolides

  2003cites this paper
• Perspectives in total synthesis: a personal account

  2003cites this paper
• Chapter 4 – Transition Metal–Carbene Complexes in Olefin Metathesis and Related Reactions

  2003cites this paper
• Synthetic Access to Epothilones‐Natural Products with Extraordinary Anticancer Activity

  2003cites this paper
• Ruthenium Catalysts for Ring-Opening Metathesis Polymerization (ROMP) and Related Chemistry

  2002cites this paper
• Alkyne metathesis: development of a novel molybdenum-based catalyst system and its application to the total synthesis of epothilone A and C.

  2001cites this paper
• SYNTHESIS OF C1–C6 FRAGMENT FOR EPOTHILONE A VIA LIPASE-CATALYZED OPTICAL RESOLUTION

  2001cites this paper
• Concise total syntheses of epothilone A and C based on alkyne metathesis

  2001cites this paper
• Catalytic antibody route to the naturally occurring epothilones: total synthesis of epothilones A-F.

  2001cites this paper
• Geminal Dimethyl-Substituted Functionalized C4-Synthons from Pantolactone

  2001cites this paper
• An Unusual Reversal of Stereoselectivity in a Boron Mediated Aldol Reaction: Enantioselective Synthesis of the C1–C6 Segment of the Epothilones

  2000cites this paper
• Subtle Variations in the Long-Range Transmission of Stereochemical Information: Matched and Mismatched Aldol Reactions This work was supported by the National Institutes of Health (Grant Nos. CA-28824 and HL-25848).

  2000cites this paper
• Enantioselective Total Synthesis of Epothilone A Using Multifunctional Asymmetric Catalyses.

  2000cites this paper
• Olefinmetathese und mehr

  2000cites this paper
• Epothilones and related structures--a new class of microtubule inhibitors with potent in vivo antitumor activity.

  2000cites this paper
• Total synthesis of epothilone B.

  2000cites this paper
• Olefin Metathesis and Beyond

  2000cites this paper
• Synthese von mittleren Ringen durch Ringschluss‐Metathese‐Reaktion

  2000cites this paper
• Combining the [2,3] sigmatropic rearrangement and ring-closing metathesis strategies for the synthesis of spirocyclic alkaloids. A short and efficient route to (±)-perhydrohistrionicotoxin

  1999cites this paper
• Reactions of complex ligands

  1999cites this paper
• Design and synthesis of constrained epothilone analogs: The efficient synthesis of eleven-membered rings by olefin metathesis

  1999cites this paper
• The chemistry of the carbon-transition metal double and triple bond: annual survey covering the year 1997

  1999cites this paper
• Ring closing metathesis as an efficient approach to branched cyclitols and aminocyclitols: a short synthesis of valiolamine

  1999cites this paper
• N‐Oxidation von Epothilon A–C und O‐Acylumlagerung zu C‐19‐ und C‐21‐substituierten Epothilonen

  1999cites this paper
• Easy Access to Both Enantiomers of C7-C12 Segment of Epothilones

  1999cites this paper
• Synthesis and biological properties of C12,13-cyclopropyl-epothilone A and related epothilones.

  1998cites this paper
• Synthesis of macrocyclic lactams and lactones via ring-closing olefin metathesis

  1998cites this paper
• Chemie und Biologie der Epothilone

  1998cites this paper
• Ringschlußmetathese von funktionalisierten Acetylen‐Derivaten: ein neuer Weg zu Cycloalkinen

  1998cites this paper
• EINE NEUARTIGE ALDOLKONDENSATION MIT 2-METHYL-4-PENTENAL UND IHR EINSATZ IN EINER VERBESSERTEN TOTALSYNTHESE VON EPOTHILON B

  1998cites this paper
• Total synthesis of 26-hydroxy-epothilone B and related analogs via a macrolactonization based strategy

  1998cites this paper
• Concise enantioselective synthesis of (+)-aspicilin based on a ruthenium catalyzed olefin metathesis reaction

  1998cites this paper
• Ring-Closing Metathesis in the Synthesis of Epothilones and Polyether Natural Products

  1998cites this paper