A5063151617- Synthesis and Reactivity of Heterocycles
- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Cyclopropane Reaction Mechanisms
- Catalytic C–H Functionalization Methods
- Synthesis and Characterization of Pyrroles
- Synthesis and pharmacology of benzodiazepine derivatives
- Marine Sponges and Natural Products
- Synthetic Organic Chemistry Methods
- Cancer therapeutics and mechanisms
- Synthesis and bioactivity of alkaloids
- Synthesis and Biological Evaluation
- Bioactive Compounds and Antitumor Agents
- Alzheimer's disease research and treatments
- Computational Drug Discovery Methods
- Chemical Synthesis and Analysis
- Traditional and Medicinal Uses of Annonaceae
- Cholinesterase and Neurodegenerative Diseases
- Multicomponent Synthesis of Heterocycles
- Oxidative Organic Chemistry Reactions
- Chemical synthesis and alkaloids
- Asymmetric Synthesis and Catalysis
- Crystallography and molecular interactions
- Click Chemistry and Applications
- Synthesis of Indole Derivatives
Yonsei University
2016-2025
Incheon National University
2024
Government of the Republic of Korea
2015-2021
Incheon Medical Center
2015
Iowa State University
2003-2011
Korea Institute of Science & Technology Information
2007-2010
Korea Research Institute of Chemical Technology
2007-2010
University of Wisconsin–Madison
2005
A new synthetic route to indolizines with various substituents on the pyridine moiety was developed by utilizing a facile cycloaromatization of 2-acetylpyrrole derivatives. Without isolation, resulting intermediates were allowed react electrophiles afford range indolizines. In particular, Suzuki–Miyaura cross-coupling O-triflates (hetero)arylboronic acids permitted introduction diverse at C8 position an indolizine skeleton.
A highly efficient [4 + 2] annulation route to polysubstituted indolizines is described employing a domino Knoevenagel condensation/intramolecular aldol cyclization process as key step. Construction of pyridine rings in indolizine skeleton was rapidly achieved from several pyrrole-2-carboxaldehydes good excellent yields, leading with various substituents at the 5, 6, and 7 positions depending on reacting active methylene partners.
A highly practical route to oligostilbenoid natural products is described. regioselective Bi(OTf)3-catalyzed cyclodehydration provided ready access 3-arylbenzofuran. Pd-catalyzed direct C–H activation of benzofuran and subsequent cross-coupling with aryl halide was successfully implemented for the introduction group at C2 position benzofuran. Further manipulation 2,3-diarylbenzofuran led efficient total synthesis permethylated analogues viniferifuran, malibatol A, shoreaphenol.
Fluorescence-based technologies play a pivotal role in various biomedical applications. Here we report an efficient route to new class of fluorophores, indolizino[3,2-c]quinolines, via the oxidative Pictet–Spengler cyclization strategy. The condensation several 2-methylpyridines with 2-bromo-2′-nitroacetophenone allowed for rapid assembly indolizines 2-nitrophenyl group at C2 position. subsequent reduction nitro under mild conditions followed by aryl aldehydes presence catalytic amount FeCl3...
Described herein is a highly efficient total synthesis of brazilin from commercially available starting materials in 9 steps with 70% overall yield. Mitsunobu coupling followed by In(III)-catalyzed alkyne-aldehyde metathesis allowed for rapid construction core skeleton quantitative Subsequent modulation oxidation levels and acid-catalyzed cyclization led to the trimethyl ether brazilin. Asymmetric dihydroxylation key intermediate was also demonstrated, which would permit asymmetric access...
ADVERTISEMENT RETURN TO ISSUEPREVLetterNEXTSynthetic Approach to Malibatol AGeorge A. Kraus and Ikyon KimView Author Information Department of Chemistry, Iowa State University, Ames, 50011 Cite this: Org. Lett. 2003, 5, 8, 1191–1192Publication Date (Web):March 20, 2003Publication History Received31 December 2002Published online20 March 2003Published inissue 1 April 2003https://pubs.acs.org/doi/10.1021/ol027574ohttps://doi.org/10.1021/ol027574orapid-communicationACS PublicationsCopyright ©...
A highly efficient total synthesis of diptoindonesin G is described employing a domino dehydrative cyclization/intramolecular Friedel−Crafts acylation/regioselective demethylation reaction aryloxyketone 7 by the action BCl3 wherein tetracyclic 6H-anthra[1,9-bc]furan-6-one skeleton was constructed via 3-arylbenzofuran in one-pot manner. This first example strategic combination these three reactions cascade fashion. The routes presented here allow for direct access to and its analogues.
A highly efficient and atom-economical construction of 2-substituted 5-hydroxybenzofurans was accomplished by employing a platinum-catalyzed domino dienone−phenol rearrangement/5-endo-dig cyclization reaction quinols bearing alkynes.
A highly efficient palladium-catalyzed α-arylation of aryloxyketones has been developed, allowing for facile installation various (hetero)aryl groups at C2 position in good to excellent yields. Subsequent cyclodehydration the resulting α-arylated provided rapid access diverse 2,3-disubstitured benzofurans.
GPR119 has emerged as a promising target for treating type 2 diabetes and associated obesity, its stimulation induces the secretion of glucagon-like peptide-1 glucose-dependent insulinotropic peptide in intestinal tract well release insulin pancreatic β-cells. We describe design synthesis novel agonists containing 1,4-disubstituted cyclohexene scaffold. Compound 21b displayed nanomolar potency (EC50 = 3.8 nM) hGPR119 activation demonstrated hypoglycemic efficacy 17.0% an oral glucose...
A highly efficient assembly of a new indolizine‐pyrrolodiazepine hybrid skeleton was achieved from one‐pot three‐component coupling pyridine‐2‐acetonitrile, N‐substituted pyrrole‐2‐carboxaldehyde, and TMSCN in the presence DBU through domino aldol condensation‐Michael addition‐cycloisomerization‐imine formation sequence which allowed for consecutive construction two central rings (pyrrole diazepine) tetracyclic product with C‐C C‐N bonds
A direct one-pot approach to polysubstituted indolizinones from tertiary propargylic alcohols using a palladium-catalyzed domino process involving aminopalladation, reductive elimination, and 1,2-shift is described.
The strategic use of a sequential Sonogashira coupling/intramolecular alkyne–carbonyl metathesis process for the synthesis pyridine ring from 1-(2-haloaryl)-1<italic>H</italic>-pyrrole-2-carbaldehydes allowed ready access to diverse novel benzo-fused indolizines, pyrrolo[1,2-<italic>a</italic>]quinolines, in good excellent yields.
Attempted cyclization of indolizines bearing both formyl and alkyne groups under acid catalysis provided benzo[e]pyrido[1,2-a]indoles with an aryl substituent at the C6 position as major products, along expected C5-acylated minor ones, which resulted from preferential deformylative intramolecular hydroarylation instead intended alkyne-carbonyl metathesis.
A highly convergent synthetic approach to rotenoid natural products is described. Successful pairing of two building blocks for Sonogashira cross-coupling and intramolecular alkyne carbonyl metathesis allows ready access 4-acylchromene, a key substructure these products, leading syntheses (±)-deguelin (±)-munduserone in high overall yields.