Total Syntheses of (−)- and (+)-Boronolide and Their Plant Growth-Inhibitory Activity

スポンサーリンク

概要

• 論文の詳細を見る

• Optically pure (+)- and (−)-boronolides were stereoselectively synthesized from yeast reductive products which had been obtained by yeast reduction of one common racemic substrate. The lactone structure of boronolide was constructed by Baeyer-Villiger oxidation. The stereochemistry of the yeast reduction products was studied to obtain the stereocenters at 5 positions of the dodecanolides of (+)- and (−)-boronolides. The stereochemistry of the 6 and 7 positions was obtained by AD-mix-α or β oxidation. The chiral center at the 8 position was constructed by employing (R)-(+)- or (S)-(−)-2-methyl-CBS-oxazaborolidine reduction or the Mitsunobu reaction. The plant growth-inhibitory activity against Echinochloa crusgalli L. of naturally occurring (+)-boronolide was higher than that of the (−)-boronolide.

著者

• YAMAUCHI Satoshi

  Faculty of Agriculture, Ehime University

• Shuto Yoshihiro

  Faculty Of Agriculture Ehime University

• Nishiwaki Hisashi

  Faculty Of Agriculture Ehime University

• Yamauchi Satoshi

  Faculty Of Agriculture Ehime University

• TSUDA Tomoko

  Faculty of Agriculture, Ehime University

• ISOZAKI Yasuyoshi

  Faculty of Agriculture, Ehime University

• NISHIMURA Hiroki

  Faculty of Agriculture, Ehime University

関連論文

• Antifungal Activity of Morinol B Derivatives of Tetrahydropyran Sesquilignan
• Antimicrobial Activity of Stereoisomers of Morinols A and B, Tetrahydropyran Sesquineolignans
• Stereoselective Construction of Tetra-Substituted Tetrahydrofuran Compounds from Benzylic Hemiacetal in the Presence of H2 and a Pd Catalyst: Stereoselective Synthesis of a Stereoisomer of (−)-Virgatusin and Its Antimicrobiological Activity
• Immunostimulation Effect of Jellyfish Collagen
• Antibacterial Activity of a Virgatusin-Related Compound
• Antifungal Activity of Tetra-Substituted Tetrahydrofuran Lignan, (−)-Virgatusin, and Its Structure-Activity Relationship
• Antimicrobiological Activity of Lignan: Effect of Benzylic Oxygen and Stereochemistry of 2,3-Dibenzyl-4-butanolide and 3,4-Dibenzyltetrahydrofuran Lignans on Activity
• Effect of Benzylic Oxygen on the Cytotoxic Activity for Colon 26 Cell Line of Phenolic Lignans
• Radical and Superoxide Scavenging Activities of Matairesinol and Oxidized Matairesinol
• Absolute Configuration of Volicitin from the Regurgitant of Lepidopteran Caterpillars and Biological Activity of Volicitin-Related Compounds
• The Effect of Secoisolariciresinol on 3T3-L1 Adipocytes and the Relationship between Molecular Structure and Activity
• Mode of Action of the Immunostimulatory Effect of Collagen from Jellyfish
• Affinity to the Nicotinic Acetylcholine Receptor and Insecticidal Activity of Chiral Imidacloprid Derivatives with a Methylated Imidazolidine Ring
• Synergistic Antioxidative Effects of Porphyrin Derivatives with α-Tocopherol and Ascorbic Acid
• Enhanced Sequence Coverage in Tryptic Fragment Analysis by Two-Dimensional HPLC/MS Using a Monolithic Silica Capillary Column
• First Stereoselective Synthesis of meso-Secoisolariciresinol and Comparison of Its Biological Activity with (+) and (−)-Secoisolariciresinol
• Immunomodulatory Effect of (−)-Matairesinol in Vivo and ex Vivo
• Inhibition of the Discoloration of Yellowtail Dark Muscle by Lignan
• Total Synthesis of (+)-Paulownin
• Total Synthesis of (+)-Phrymarolin I from (+)-Malic Acid
• IgE-Suppressive Activity of (-)-Matairesinol and Its Structure-Activity Relationship
• Effects of Batatasin III and Its Analogs on Gibberellic Acid-Dependent α-Amylase Induction in Embryoless Barley Seeds and on Cress Growth
• Antifungal Activity of Morinol B Derivatives of Tetrahydropyran Sesquilignan
• Antimicrobial Activity of Stereoisomers of Butane-Type Lignans
• Inhibition of the Discoloration of Yellowtail Dark Muscle by Lignan
• Syntheses and Antimicrobial Activity of Tetrasubstituted Tetrahydrofuran Lignan Stereoisomers
• Antimicrobial Activity of Stereoisomers of Morinols A and B, Tetrahydropyran Sesquineolignans
• The Effect of Secoisolariciresinol on 3T3-L1 Adipocytes and the Relationship between Molecular Structure and Activity
• Antioxidant Activity of Butane Type Lignans, Secoisolariciresinol, Dihydroguaiaretic Acid, and 7,7'-Oxodihydroguaiaretic Acid
• Syntheses of All Stereoisomers of Goniodiol from Yeast-Reduction Products and Their Antimicrobiological Activity
• Structure-Antibacterial Activity Relationship for 9-O,9'-O-Demethyl (+)-virgatusin
• Stereoselective Construction of Tetra-Substituted Tetrahydrofuran Compounds from Benzylic Hemiacetal in the Presence of H_2 and a Pd Catalyst : Stereoselective Synthesis of a Stereoisomer of (-)-Virgatusin and Its Antimicrobiological Activity
• First Stereoselective Synthesis of meso-Secoisolariciresinol and Comparison of Its Biological Activity with (+) and (-)-Secoisolariciresinol
• Antimicrobiological Activity of Lignan : Effect of Benzylic Oxygen and Stereochemistry of 2,3-Dibenzyl-4-butanolide and 3,4-Dibenzyltetrahydrofuran Lignans on Activity
• Antifungal Activity of Tetra-Substituted Tetrahydrofuran Lignan, (-)-Virgatusin, and Its Structure-Activity Relationship
• Antibacterial Activity of a Virgatusin-Related Compound
• Syntheses of Secocyclolignanes and Comparative Antioxidative Activity between Secocyclolignane and the Dibenzyl Type of Lignan
• Synthesis of Amino Tetrahydrofuran Lignan via an N,O-Heterocyclic Compound as an Intermediate
• Synthesis of an Optically Pure Synthetic Intermediate of Aloperine from a Yeast-Reductive Product
• Synthesis and Antioxidant Activity of Olivil-Type Lignans
• Synthesis and Antioxidant Activity of Oxygenated Furofuran Lignans
• First Diastereoselective Construction of Butane-Type and Butyrolactone-Type Secocyclolignane Structures
• Improved Procedure for the Enantiometric Synthesis of 1-Hydroxy/acetoxy-2,6-diaryl-3,7-dioxabicyclo [3 .3. 0] octane Lignans : Total Syntheses of (+)-Paulownin, (+)-Phrymarin I and (+)-Phrymarin II
• Improved Syntheses of Morinol C and D by Employing Mizoroki-Heck Reaction and Their Cytotoxic and Antimicrobial Activities
• Mode of Action of the Immunostimulatory Effect of Collagen from Jellyfish
• Use of the Benzyl Mesylate for the Synthesis of Tetrahydrofuran Lignan: Syntheses of 7,8-trans, 7′,8′-trans, 7,7′-cis, and 8,8′-cis-Virgatusin Stereoisomers
• Immunomodulatory Effect of (-)-Matairesinol in Vivo and ex Vivo
• Larvicidal Activity of (−)-Dihydroguaiaretic Acid Derivatives against Culex pipiens
• Effect of the Benzylic Structure of Lignan on Antioxidant Activity
• Syntheses of Secocyclolignanes and Comparative Antioxidative Activity between Secocyclolignane and the Dibenzyl Type of Lignan
• Disruption of Ion Homeostasis by Verrucosin and a Related Compound
• Pyropheophytin a as an Antioxidative Substance from the Marine Alga, Arame (Eisenia bicyclis)
• Synthesis of a Glandular Secretion of the Civet Cat, (2S,6S)-(6-Methyltetrahydropyran-2-yl)acetic Acid and Its Enantiomer, by Using the Yeast-Reduction Product and Recovered Substrate from Yeast Reduction
• Syntheses of (+)- and (-)-Dihydropinidine and (+)- and (-)-Epidihydropinidine by Using Yeast Reduction of Methyl (2-oxocyclohexyl)acetate
• Effect of Optically Active Ethyl 2-Phthalimidooxypropionate on the Growth of Cress, Lepidium sativum
• Antioxidative Activity of Porphyrin Derivatives
• Affinity to the Nicotinic Acetylcholine Receptor and Insecticidal Activity of Chiral Imidacloprid Derivatives with a Methylated Imidazolidine Ring
• New Method for Synthesizing the Intermediates to 5-HETE from Yeast-mediated Reduction Products by Employing Baeyer-Villiger Oxidation with Complete Retention of Enantiomeric Excess(Organic Chemistry)
• Stereoselective Synthesis of the Neolignan, (+)-Dehydrodiconiferyl Alcohol
• Larvicidal Activity of (-)-Dihydroguaiaretic Acid Derivatives against Culex pipiens
• Total Syntheses of (−)- and (+)-Boronolide and Their Plant Growth-Inhibitory Activity
• Total Syntheses of (-)- and (+)-Boronolide and Their Plant Growth-Inhibitory Activity

もっと見る 閉じる

スポンサーリンク