Total Synthesis of Madindoline A
スポンサーリンク
概要
- 論文の詳細を見る
The total synthesis of madindolin A was achieved. Stereoselective construction of the quaternary carbon in the cyclopentenedione moiety was accomplished by alkylation of dienolate bearing a chiral auxiliary. The coupling of sterically hindered aldehyde 17 and acid-sensitive amine 30 was achieved by developing a new reductive amination method using Sn (OTf)<SUB>2</SUB> and NaBH(OAc)<SUB>3</SUB>. After the reductive coupling, the cyclopentenedione skeleton of madindoline was constructed by intramolecular condensation of triketone 5.
- 社団法人 有機合成化学協会の論文
- 2001-11-01
著者
-
KOBAYASHI Susumu
Faculty of Pharmaceutical Sciences, Science University of Tokyo
-
Kobayashi Susumu
Faculty Of Pharmaceutical Sciences Science University Of Tokyo
-
HOSOKAWA Seijiro
Faculty of Science & Engineering, Waseda University
-
Hosokawa Seijiro
Faculty Of Pharmaceutical Sciences Science University Of Tokyo
関連論文
- Lariatins, Novel Anti-mycobacterial Peptides with a Lasso Structure, Produced by Rhodococcus jostii K01-B0171
- Deacetylravidomycin M, a New Inhibitor of IL-4 Signal Transduction, Produced by Streptomyces sp. WK-6326 : I. Taxonomy, Fermentation, Isolation and Biological Activities
- Synthetic Studies of Zoanthamine/Norzoanthamine : Biogenetic-like One-Step Construction of the Heterocyclic Aminal Core (CDEFG Ring) from a Monocyclic Precursor
- Glycosyl 2-Pyridinecarboxylate as an Effective Glycosyl Donor : Glycosidation of Mannose, 2-Azidosugar, and 2-Deoxysugar into Disaccharides
- Synthesis of Fluorescence-Labeled Galβ1-3Fuc and Galβ1-4Fuc as Probes for the Endogenous Glyco-Epitope Recognized by Galectins in Caenorhabditis elegans
- Cholesteryl Glucoside-induced Protection against Gastric Ulcer
- Stereoselective Route to the Highly Oxidated Sidechain Moiety of Terpentecin and Related Antibiotics
- New Antibiotics Miyakamides Produced by a Fungus
- Synthesis of Pseudodeflectusin and Ustusorane C: Structural Revision of Aspergione A and B
- YCM1008A, a Novel Ca^-Signaling Inhibitor, Produced by Fusarium sp. YCM1008
- Stereoselective Vinylogous Mukaiyama Aldol Reaction of α-Haloenals
- Novel Biological Activity of the Region (106-126) on Human Prion Sequence
- Biological Activities of 1,1,6-Trisubstituted Indanes : Beyond Magainin 2
- Antibacterial Activity of (±) 6-Benzyl-1-(3-carboxypropyl) indane; A Possible Way to Identify Leading Novel Anti-H. pylori Agents
- Antibacterial Activity of Two Alkylamines Integrated an Indane Scaffold : Mimicry of a Complementary Unit on Magainin 2
- Inhibitory Effect of Sulfoquinovosyl Diacylglycerol on Prokaryotic DNA Polymerase I Activity and Cell Growth of Escherichia coli
- Steryl Glucoside is a Lipid Mediator in Stress-responsive Signal Transduction
- P-468 A Novel Ryanodine Binding Inhibitor, Verticilide, Produced by Verticilium sp. FKI-1033
- A New Antibiotic, Antimycin A_9, Produced by Streptomyces sp. K01-0031
- New Beauveriolides Produced by Amino Acid-supplemented Fermentation of Beauveria sp. FO-6979
- Deacetylravidomycin M, a New Inhibitor of IL-4 Signal Transduction, Produced by Streptomyces sp. WK-6326 : II. Structure Elucidation
- Selective Production of Fungal Beauveriolide I or IIIby Fermentation in Amino Acid-supplemented Media
- Synthetic Study on Telomerase Inhibitor, D8646-2-6 : Synthesis of the Key Intermediate Using Sn (OTf)_2 or Sc (OTf)_3 Mediated Aldol-Type Reaction and Stille Coupling
- Total Synthesis of Madindoline A
- A Possible Mechanism of Cholesteryl Glucoside Formation Involved in Heat Shock Response in the Animal Cell Membrane
- Synthesis of Pseudodeflectusin and Ustusorane C : Structural Revision of Aspergione A and B
- Comparison of Inhibitory Activities of Stereo-Isomers of Cyclic Phosphatidic Acid (cPA) on Autotaxin
- K97-0239A and B, new inhibitors of macrophage foam cell formation, produced by Streptomyces sp. K97-0239
- Stereocontrolled Total Synthesis of (-)-Gleenol Using Claisen Rearrangement of Sterically Congested Dihydropyran
- Total Synthesis of (±)-Gleenol and (±)-Axenol via a Functionalized Spiro[4.5]decane
- Claisen Rearrangement Strategy in Alkenyl Dihydropyran Leading to Total Synthesis of (+)-α-Vetispirene and (-)-Agarospirol
- A PhSeCl-Mediated Allylic Oxidation of Prenyl Moiety : A Convenient Method for the Construction of 3-Isopenten-2-ol Unit
- The first total synthesis of nidulalin A, a dihydroxanthone possessing multiple bioactivities
- Verticilide, a new ryanodine-binding inhibitor, produced by Verticillium sp. FKI-1033
- Determination of the Absolute Structure of (+)-Akaterpin
- Deprotection of the Methoxymethyl Group on 3-Spiro-2-oxindole under Basic Conditions
- Asymmetric Hydrolysis of Prochiral Dimethyl 3-Benzyloxycarbonylaminoglutarate with Microorganisms. Preparation of (S)-3-Amino-4- methoxycarbonylbutyric Acid for the Synthesis of Carbapenem and Negamycin Antibiotics