A Short Synthesis of Methylenomycin B by the Nazarov Reaction

Motoyoshiya, Jiro; Mizuno, Kazumasa; Tsuda, Tomoya; Hayashi, Sadao

doi:10.1055/s-1993-22417

Cited by 10 publications

(1 citation statement)

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“…2-Cyclopentenones are five membered carbocycles consisting of α,β-unsaturated ketone system. Cyclopentenone and its derivatives are important motifs in synthetic organic chemistry as they are useful key intermediates in total synthesis 1,2 of natural products like methylenomycin B 3 , a natural cyclopentanoid antibiotic, ligands of the 5HT 1D serotonin receptors 4 , prostaglandin 5 , etc.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Evaluation of Some Substituted-3-Aryl -2,3,4,5,6,7-hexahydro-1H-inden-1-one

2014

Chem Sci Trans

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Synthesis of new cyclopentenone derivatives by reacting 1-acetyl-1-cyclohexene with various aromatic and heteroaromatic aldehydes is reported. All the new cyclopentenone derivatives were characterized by 1 H, 13 C NMR, IR and mass spectral data, and were further screened for their antimicrobial activity. Most of the compounds showed comparable activities with standard drug ciprofloxacin and in particular, compounds 3d, 3f, 3g and 3j showed excellent activity against all the four bacterial strains.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Evaluation of Some Substituted-3-Aryl -2,3,4,5,6,7-hexahydro-1H-inden-1-one

2014

Chem Sci Trans

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Nazarov Cyclization

2010

Comprehensive Organic Name Reactions and Reagents

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Nazarov cyclization, or Nazarov reaction is an acid‐promoted cationic pericyclic reaction that transforms a divinyl ketone into 2‐cyclopentenone. This reaction undergoes a 4‐π electrocyclic, conrotatory cyclization via a 3‐oxy‐pentadienylic cation and requires of strong Brønsted acid or Lewis acid. Many complicated Lewis acids have been used for this reaction. This reaction gives a thermodynamically favored cyclopentenone with more substituents. Alkoxy on a vinyl group, or the presence of a bridge‐headed proton on the endocyclic intermediate facilitates the protic acid‐promoted cyclization. Denmark has developed the directed Nazarov cyclization and Ichikawa has developed the other form to control the regiochemistry. The interrupted Nazarov reaction has also been developed to extend the reaction of the cationic endocyclic intermediate with carbon nucleophiles.

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Formation of Aldehydes and Ketones by Rearrangements

Larock

Dubrovskiy

Markina

2018

Comprehensive Organic Transformations

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Isomerization Epoxides Vinylic Ethers Pinacol and Related Rearrangements Ring Rearrangement Ring Opening Ring Contraction Ring Expansion Electrocyclic Rearrangements Miscellaneous Rearrangements

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A Short Synthesis of Methylenomycin B by the Nazarov Reaction

Cited by 10 publications

References 0 publications

Synthesis and Antimicrobial Evaluation of Some Substituted-3-Aryl -2,3,4,5,6,7-hexahydro-1H-inden-1-one

Synthesis and Antimicrobial Evaluation of Some Substituted-3-Aryl -2,3,4,5,6,7-hexahydro-1H-inden-1-one

Nazarov Cyclization

Formation of Aldehydes and Ketones by Rearrangements

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