Diene, Enyne, and Diyne Metathesis in Natural Product Synthesis

Mulzer, Johann; Öhler, Elisabeth

doi:10.1002/chin.200546264

Cited by 3 publications

(3 citation statements)

References 114 publications

(186 reference statements)

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“…Olefin metathesis is a highly valuable tool in the hands of a synthetic chemist and has been a subject of numerous studies in very divergent fields of chemistry . Most common classes of metathesis reaction include ring-opening metathesis polymerization (ROMP), ring-closing metathesis (RCM), ring-opening metathesis (ROM), acyclic diene metathesis (ADMET), and cross-metathesis (CM) . Metathesis assumes additional significance when directed toward bicyclic systems as substrates because they offer opportunities for incorporating additional structural complexity in the desired product.…”

Section: Applications Of Vince Lactammentioning

confidence: 99%

2-Azabicyclo[2.2.1]hept-5-en-3-one: Chemical Profile of a Versatile Synthetic Building Block and its Impact on the Development of Therapeutics

2012

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| Chem. Rev. 2012, 112, 4642−4686 4.4.3. Enantioselective Synthesis of Various Heterocyclic Compounds via ROM-RCM Domino Metathesis of Ring-Opened Vince Lactam Derivatives 4669 4.5. Use of Vince Lactam as a Standard in Chemical Analysis of Compounds and Optical Activity of Stereoisomers 4669 5. Conclusions 4669 Author Information 4669 Corresponding Author 4669 Notes 4669 Biographies 4670 Acknowledgments 4670 Abbreviations 4670 References 4671V). The well-known preference of the hydrolase enzymes to attack a substrate from si face rather than re face was studied in the system via molecular modeling of the two tetrahedral intermediates. These studies revealed that the complexes modeled on re face for both the isomers of the racemate were highly unfavorable. Furthermore, the unpropitious steric Scheme 12. Biocatalytic Resolution of Vince Lactam Followed by Various Chemical Transformations to Obtain the Desired Stereoisomers of Synthetic Intermediates Scheme 13. Proposed Mechanistic Pathway for the Biocatalytic Hydrolysis of Vince Lactam Chemical Reviews Review dx.

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Section: Applications Of Vince Lactammentioning

confidence: 99%

2-Azabicyclo[2.2.1]hept-5-en-3-one: Chemical Profile of a Versatile Synthetic Building Block and its Impact on the Development of Therapeutics

2012

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“…[1][2][3][4][5][6][7][8][9][10][11] Initially, the scope and applications of this type of reaction was limited by the poor functional group tolerance that the catalysts had. However, over the past few years more robust, functionality-tolerant and highly reactive metathesis catalysts have been developed extending the scope of this transformation to a wide range of olefinic substrates.…”

Section: Introductionmentioning

confidence: 99%

Phenylphosphoric Acid as a New Additive to Inhibit Olefin Isomerisation in Ruthenium‐Catalysed Metathesis Reactions

et al. 2007

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A systematic study of the ruthenium-catalysed metathesis of alkenes containing hydrogen-bonding substituents (namely urea and thiourea groups) is presented. Under standard metathesis conditions, several of the substrates under study undergo alkene isomerisation instead of the targeted metathesis. However, in the course of these investigations it has been established that this unwanted isomerisation process can be suppressed by addition of phenylphosphoric acid to the reaction mixture. Some other potential isomerisation inhibitors (e.g. benzoic acid and salts of phosphoric acid) have been

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“…The Mo and Ru carbenes are transition metal catalysts which can perform a variety of metathesis reactions among alkene, alkyne and allene substrates. The diversity of Mo- and Ru-based metathesis reactivity is reflected by the presence of numerous metathesis reactions including olefin metathesis, enyne metathesis, allene metathesis, diyne metathesis, and allenyne metathesis …”

Section: Introductionmentioning

confidence: 99%

Quantitative Catalyst−Substrate Association Relationships between Metathesis Molybdenum or Ruthenium Carbene Complexes and Their Substrates

Kim

Lee

et al. 2010

J. Am. Chem. Soc.

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Herein we present the long-sought quantitative catalyst-substrate association relationships based on experimentally measured quantitative association preferences of diverse metathesis Mo and Ru catalysts (Mo-1, Schrock Mo; Mo-2, Schrock-Hoveyda Mo; Ru-1, Grubbs first generation Ru; Ru-2, Grubbs second generation Ru; Ru-3:, Grubbs-Hoveyda first generation Ru; and Ru-4, Grubbs-Hoveyda second generation Ru) to their substrates (alkenes, alkynes and allenes), determined directly by a general method based on FRET principle. The determined substrate preferences are proved to be dependent on the molecular identity of the catalyst, exhibiting the preference order of alkyne > alkene > allene for Mo-1 and Mo-2, allene > alkene > alkyne for Ru-1 and Ru-3, and alkyne > allene > alkene for Ru-2 and Ru-4. The results enable us to probe metathesis mechanisms by answering issues in metathesis reactions including the controversial reaction initiation in enyne or allenyne metathesis.

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Diene, Enyne, and Diyne Metathesis in Natural Product Synthesis

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 3 publications

References 114 publications

2-Azabicyclo[2.2.1]hept-5-en-3-one: Chemical Profile of a Versatile Synthetic Building Block and its Impact on the Development of Therapeutics

2-Azabicyclo[2.2.1]hept-5-en-3-one: Chemical Profile of a Versatile Synthetic Building Block and its Impact on the Development of Therapeutics

Phenylphosphoric Acid as a New Additive to Inhibit Olefin Isomerisation in Ruthenium‐Catalysed Metathesis Reactions

Quantitative Catalyst−Substrate Association Relationships between Metathesis Molybdenum or Ruthenium Carbene Complexes and Their Substrates

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