A Convenient Synthesis of 5-Substituted-2,5-dihydro-2-furoic Acids
スポンサーリンク
概要
- 論文の詳細を見る
Nine 5-alkyl- and 5-aryl-2-furoic acids were reduced under controlled Birch conditions and then esterified with acidic methanol. 2-Furoic acids with 5-alkyl groups gave good yields of methyl 5-alkyl-2,5-dihydro-2-furoates, which were obtained as mixtures of <I>cis</I>- and <I>trans</I>-diastereoisomers. These 2,5-dihydrofuroates revealed interesting spectroscopic properties; (1) large long-range coupling constants, 5–7 and 3–4 Hz, between protons at C<SUB>2</SUB> and C<SUB>5</SUB> were observed in the NMR spectra of <I>cis</I>- and <I>trans</I>-diastereoisomers, respectively, and (2) two high absorption maxima due to the ester carbonyl group of each furoate appeared near 1750 and 1730 cm<SUP>−1</SUP> in the IR spectrum. On the other hand, the furoic acids with 5-aryl substituents afforded 5-arylpentanoate or 5-arylpent-3-enoate as main products. These esters would be produced as a result of reductive cleavage at C<SUB>5</SUB> of 5-aryl-2,5-dihydrofuroates formed as intermediates.
- 公益社団法人 日本化学会の論文
著者
-
Masamune Tadashi
Department Of Chemistry Faculty Of Science Hokkaido University
-
Matsue Hajime
Department Of Cardiovascular Medicine Kyoto Prefectural University School Of Medicine
-
Ono Mitsunori
Department of Chemistry, Faculty of Science, Hokkaido University
-
Matsue Hajime
Department of Chemistry, Faculty of Science, Hokkaido University
関連論文
- PE-321 Assessment of Local Myocardial Stress and Function in Ischemic Cardiomyopathy : New Method Using Multidetector Computed Tomography and Novel Software System(PE054,CT/MRI (New Technology) (I),Poster Session (English),The 73rd Annual Scientific Meeti
- OJ-155 Assessment of Regional Myocardial Stress before and after Restrictive Mitral Annuloplasty for Dilated Cardiomyopathy with Novel Software System(OJ26,Cardiac Function (Clinical) (M),Oral Presentation (Japanese),The 73rd Annual Scientific Meeting of
- PJ-082 Assessment of Left Atrial Transport Function after the Maze Procedure Using Magnetic Resonance Imaging(Cardiac function, basic/clinical-3, The 71st Annual Scientific Meeting of the Japanese Circulation Society)
- PD27 HYDROGEN PEROXIDE ACTS AS AN ENDOGENOUS ELICITOR FOR PHYTOALEXIN PRODUCTION
- Isolation of an Endogenous Elicitor Induced by Hydrogen Peroxide from Potato
- Hydrogen Peroxide as a Dynamic Trigger for Phytoalexin Production
- Biological activities of rishitin, an antifungal compound isolated from diseased potato tubers, and its derivatives
- E-10-1 Structure of _α-Cholestanol(Steroids)
- The structure and configuration of (+)-glutionosone and (+)-oxyglutinosone.
- Phytosterols and Triterpenes in the Roots of the "Kidney Bean" (Phaseolus vulgaris L.)
- Synthetic studies of laurencin and related compounds. IV. Synthesis of cis-2-ethyl-8-formyl-3,4,7,8-dihydro-2H-oxocin-3-one 3-ethylene acetal and related compounds.
- A Convenient Synthesis of 5-Substituted-2,5-dihydro-2-furoic Acids
- Photo-induced radical rearrangements of hypoiodite of N-acetyljervine and the related C-nor-D-homosteroid in the presence of mercury(II) oxide and iodine.
- Structure of rishitione, a valencane stress metabolite in diseased potato.
- Synthesis of .BETA.- and .ALPHA.-rotunols. Revision of the structure of a stress metabolite "1-keto-.ALPHA.-cyperone".
- Structure of epilubimin, epioxylubimin, and isolubimin, spirovetivane stress metabolites in diseased potato.
- The transformation of jervine into 18-functional D-homo-C-norsteroids. IV. The transformation of jervine into (20R)-18,20.BETA.-epoxy-3.BETA.-hydroxy-17.BETA.-ethyletiojervan-18-one 3-acetate via (20R)-18,20.BETA.-epoxy-3.BETA.-hydroxy-12.ALPHA.,17.BETA.-
- Synthesis and photoreaction of D-nor-5.ALPHA.-androstan-16-one acetylhydrazone in the presence of oxygen.
- Synthesis of phytuberin.
- Total synthesis of (.+-.)-lubimin and (.+-.)-oxylubimin. II. Transformation of (.+-.)-15-norsolavetivanes into (.+-.)-lubimin, (.+-.)-oxylubimin, and related compounds.
- The Structure and Synthesis of Rishitinol. A Sesquiterpene Alcohol from Diseased Potato Tubers
- Synthetic Studies of Laurencin and Related Compounds. I. The Synthesis of t-3-Bromo-r-2,c-8-diethyl-3,4,7,8-tetrahydro-2H-oxocin
- Photooxygenation of .ALPHA.,.BETA.- and .BETA.,.GAMMA.-unsaturated enamines in 17-(1-formylethyl)etiojervanes.
- Stereochemistry of the C and D rings of C-nor-D-homosteroid. IV. The relative stabilities and NMR spectra of 17-substituted C/D trans- and cis-fused etiojervanes.
- Stereochemistry of the C and D rings of C-nor-D-homesteroids. III. The synthesis of etiojervane analogs of androstan-3.BETA.ol.
- Rishitin. I. The isolation and structure elucidation.
- 12,13-Epoxy-C-nor-D-homosteroids. VI. Reaction of 17-oxygenated 12,13-epoxyetiojervanes with boron trifluoride etherate.
- 12,13-Epoxy-C-nor-D-homosteroids. VIII. Transformation of 12.ALPHA.,13.ALPHA.-epoxyetiojerv-5-ene-3,17-dione 3,3-ethylene acetal into testosterone.
- 12,13-Epoxy-C-nor-D-homosteroids. VII. Reaction of 11-oxygenated 17.ALPHA.-acetyl-12.BETA.,13.BETA.-epoxy-13-epietiojervanes with boron trifluoride etherate and potassium hydroxide.
- Oxidation of 1-Cyclohex-1-enecarbaldehyde and Related Compounds with Caro's Acid
- Total synthesis of (.+-.)-lubimin and (.+-.)-oxylubimin. I. Synthesis of (.+-.)-15-norsolavetivone and related compounds.
- A general synthetic approach of spirovetivanes. The synthesis of (.+-.)-solavetivone, (.+-.)-hinesol, and related compounds.
- Synthesis of aubergenone, a sesquiterpenoid phytoalexin from diseased eggplants.
- Steric effect in regioselective cyclization of 3,4-epoxy alcohols to oxetanes.
- The configuration of 17-ethyl-3.BETA.-hydroxyetiojerva-5,12,17(20)-trien-11-one and related compounds.
- Synthetic studies of laurencin and related compounds. V. Transformation of cis-2-ethyl-8-formyl-3,4,7,8-dihydro-2H-oxocin-3-one 3-ethylene acetal into (.+-.)-laurencin.
- Intramolecular cyclization of 3,4-epoxy alcohols; oxetane formation.
- Stereochmistry of the C and D rings of C-nor-D-homosteroids. II. Synthesis of etiojervane analogs of pregnan-3.BETA.-ol.
- Lubimin and oxylubimin. The structure elucidation.
- 12,13-Epoxy-C-nor-D-homosteroids. III. The synthesis and stereochemistry of 17-oxygenated 12,13-epoxyetiojervanes.
- 12,13-Epoxy-C-nor-D-homosteroids. I. The synthesis and stereochemistry of 17.ALPHA.-acetyl-12,13-epoxyetiojervanes.
- The Synthesis of an Etiojervane Analog of Corticosterone.
- The photo-Beckmann rearrangement of A-nor-5.ALPHA.-cholestan-3-one oxime.
- 12,13-Epoxy-C-nor-D-homosteroids. IV. The reaction of 11-oxygenated 17.ALPHA.-acetyl-12.ALPHA.,13.ALPHA.-epoxyetiojervanes with boron trifluoride etherate.
- Angiotensin-Converting Enzyme-Inhibitory Peptides Isolated from Pepsin Hydrolyzate of Apios americana Tuber and Their Hypotensive Effects in Spontaneously Hypertensive Rats