Γ-lactone Derivatives Research Articles

Three New Compounds, Ficusone, Ficuspirolide, and Ficusolide from the Heartwood of Ficus microcarpa.

One new apocarotenoid, ficusone (1), and two novel γ-lactone derivatives, ficuspirolide (2) and ficusolide (3) as well as 4, 5-dihydrolblumenol (4), were isolated from the heartwood of Ficus microcarpa L.f. Their structures were principally determined by spectral evidence.

Synthesis of γ-lactone derivatives as a key intermediate for the spiroketal fragment in calyculin A

Abstract A simple and safe route to the D-xylone-1,4-lactone derivative 3, a key intermediate for the synthesis of the spiroketal fragment in calyculin A (1) has been explored without the use of hazardous diazomethane on a large scale.

Muridienin-1 and -2: The missing links in the biogenetic precursors of acetogenins of annonaceae

Isolation of Δ n,n+4 diunsaturated γ-lactone derivatives of lacceroic and ghedoic acids, allows us to confirm the biogenetic pathway of the bioactive acetogenins of Annonaceae.

γ-Lactones: Methyl 11-Oxa-10-oxobicyclo[6.3.0]undec-4-ene-9-carboxylate, Methyl 11-Oxa-10-oxobicyclo[6.3.0]undec-2-ene-9-carboxylate and Methyl 9-Oxa-10-oxobicyclo[6.3.0]undecane-11-carboxylate

The structures of three γ-lactone derivatives, methyl 11-oxa-10-oxobicyclo[6.3.0]undec-4-ene-9-carboxylate, C12H16O4, methyl 11-oxa-10-oxobicyclo[6.3.0]undec-2-ene-9-carboxylate, C12H16O4 and methyl 9-oxa-10-oxobicyclo[6.3.0]undecane-11-carboxylate, C12H18O4, have been solved in order to determine the relative configuration of their three asymmetric stereocentres.

Neo-clerodane diterpenoids from Scutellaria cypria

Two pairs of diastereomeric hemiacetals, scutecyprols A and B, have been detected in the aerial parts of Scutellaria cypria var. cypria. They were isolated, after oxidation, as their γ-lactone derivatives, along with the known scutecyprin.

Studies on total syntheses of antitumor styryllactones: Stereoselective total syntheses of (+)-goniofufurone, (+)-goniobutenolide A, and (−)-goniobutenolide B

A highly stereoselective aldol reaction of the aldehyde 11, derived from (+)-tricarbonyl( η 6-2-trimethylsilylbenzaldehyde)chromium(0) complex ( 4), with 2-trimethysilyloxyfuran afforded the γ-lactone derivative 13. The γ-lactone 13 was subsequently converted into three antitumor styryllactones, (+)-goniofufurone, (+)-goniobutenolide A, and (−)-goniobutenolide B.

Study of the binding affinity of oligo-tetrahydrofuranic γ-lactones with cations

Tetrahydrofuranic γ-lactone derivatives have shown interesting cytotoxic activities which can be explained by an ionophoric ability. Indeed, divalent cations show a higher affinity than monovalent ions with these lactones, with a dependancy on the stereochemical relationships of the stereogenic centres of the molecules.

Mechanism of the formation in vivo of α-phenyl-γ-lactones in the glutethimide series

The isolation of γ-lactones from the urines of humans or animals treated with glutethimide or aminoglutethimide required an explanation. The question was studied on the glutethimide model. Potential metabolites such as β-hydroxymetabolite, γ-lactone amide, and γ-lactone acid were synthesized. Glutethimide was first administered to rats at high and normal doses. The corresponding γ-lactone amide, resulting from alcoholysis of β-hydroxyglutethimide, was also administered to rats. The amounts of the various γ-lactone derivatives isolated from the urine were discussed and it was concluded that the α-phenyl-γ-lactone was formed in vivo via β-hydroxylation of glutethimide followed by intramolecular alcoholysis. The lactone amide was then oxidized and dealkylated via an intramolecular mechanism leading to the corresponding α-phenyl-γ-lactone.

A novel hepatoprotective .NU.-lactone, MH-031. I. Discovery, isolation, physico-chemical properties and structural elucidation.

A new subspecies of Streptomyces rishiriensis A-5969 (PERM BP-1394) was isolated and shown to produce a novel α, β-unsaturated γ-lactone derivative, MH-031, which exhibited hepatoprotective activity in primary cultured rat hepatocytes intoxicated with D-galactosamine.

(±)-erythro-γ,δ-Dihydroxycarboxylic Acid Lactones from a β-Lithiopropionate Equivalent and α-Chloroaldehydes

Reaction of β-ethylthio-β-lithioacrylate with α-chloroaldehydes furnished predominantly the erythro products I, which were isolated as γ-lactones; At room temperature intermediates I are transformed into the (±)-erythro-γ,δ-dihydroxycarboxylic acid γ-lactones. Raney nickel treatment provided interesting natural γ-lactone derivatives

ChemInform Abstract: Complexing Ability of Some γ-Lactone Derivatives. Thermal, Magnetic and Spectral Studies on Cobalt(II), Nickel(II) and Copper(II) Complexes and Their Base Adducts.

The reaction of an ammoniacal solution of hydrated Co, Ni or Cu chloride with an ethanolic solution of the corresponding lactone under reflux gives the complexes (I) (no yields given), containing 2 or 3 mol of water being partially hydrogen-bonded to the coordinated ligands.

Complexing ability of some γ-lactone derivatives. Thermal, magnetic and spectral studies on cobalt(II), nickel(II) and copper(II) complexes and their base adducts

The complexes of some γ-lactone derivatives with cobalt(II), nickel(II) and copper(II) have been synthesized and formulated as [ML 2]· nH 2O, M = Co 2+, Ni 2+ or Cu 2+, n = 2 or 3 and L = anion of the corresponding ligand. Their structures have been suggested on the basis of analysis, spectral (UV-Vis, IR) and magnetic susceptibility data. The thermal analysis revealed the non-coordinated water among these complexes. The infrared spectra show the existence of water molecules involved in a hydrogen-bonding with the coordinated ligands and the γ-lactones are mono-basic bidentate coordinated to the metal ion via the benzoyl carbonyl and the deprotonated hydroxylic oxygen atoms. The bulkiness and the electronic properties of the lactones on the structure of the complexes are rationalized from the electronic spectral data. The interaction of the complexes with different Lewis basis is studied spectrophotometrically. The ligand field parameters are calculated and related to the bulkiness effect of the ligand molecules. These parameters indicate the axial ligation of the base molecules and that the equatorial plane is occupied by the MO 4, M = Co 2+, Ni 2+ or Cu 2+, chromophore. The interelectronic repulsion parameter indicates the ionic nature of these complexes. The extent of distortion from the idealized structure is also discussed.

ChemInform Abstract: New α-Methylene γ-Lactone Derivatives of Substituted Nucleic Acid Bases as Potential Anticancer Agents.

ChemInform Abstract: New α-Methylene γ-Lactone Derivatives of Substituted Nucleic Acid Bases as Potential Anticancer Agents.

Additions and Corrections - New α-Methylene γ-Lactone Derivatives of Substituted Nucleic Acid Bases as Potential Agents.

Additions and Corrections - New α-Methylene γ-Lactone Derivatives of Substituted Nucleic Acid Bases as Potential Agents.

ChemInform Abstract: STEREOCHEMISTRY OF RINGS. XV. Γ‐LACTONE DERIVATIVES. PART 9. X‐RAY STRUCTURE OF 5‐CHLOROMETHYL‐2‐OXAZOLIDINONE

Chemischer InformationsdienstVolume 16, Issue 10 Physical Organic Chemistry ChemInform Abstract: STEREOCHEMISTRY OF RINGS. XV. Γ-LACTONE DERIVATIVES. PART 9. X-RAY STRUCTURE OF 5-CHLOROMETHYL-2-OXAZOLIDINONE G. BOCELLI, G. BOCELLISearch for more papers by this authorM.-F. GRENIER-LOUSTALOT, M.-F. GRENIER-LOUSTALOTSearch for more papers by this author G. BOCELLI, G. BOCELLISearch for more papers by this authorM.-F. GRENIER-LOUSTALOT, M.-F. GRENIER-LOUSTALOTSearch for more papers by this author First published: March 12, 1985 https://doi.org/10.1002/chin.198510064AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume16, Issue10March 12, 1985 RelatedInformation

Stereochemistry of rings, XV. γ-Lactone derivatives: Part 9. X-ray structure of 5-chloromethyl-2-oxazolidinone

C 4H 5NO 2Cl ( M r = 135.55) crystallizes in the monoclinic system, space group P2 1 ie with a = 9.257(2), b = 5.181(3), c = 12.620(2) A, β = 110.75(4)°, V = 566.0(4) A 3, Z = 4, D c = 1.59 g cm −1, μ(Cu Kα) = 53.16 cm −1, γ = 1.5418 A, F(000) = 280. The oxazolidinone ring is approximately planar; the geometrical parameters reveal a certain degree of electronic delocalization in the molecule. The CH 2Cl group assumes an axial position. The molecules are joined in dimers by strong N—H ⋯.. O hydrogen bonds.

ChemInform Abstract: STEREOCHEMISTRY OF RINGS. XII. Γ‐LACTONE DERIVATIVES. PART 7. THE X‐RAY STRUCTURE OF 3‐ACETYLAMINO‐2‐THIOLANONE

Chemischer InformationsdienstVolume 14, Issue 9 Physical Organic Chemistry ChemInform Abstract: STEREOCHEMISTRY OF RINGS. XII. Γ-LACTONE DERIVATIVES. PART 7. THE X-RAY STRUCTURE OF 3-ACETYLAMINO-2-THIOLANONE G. BOCELLI, G. BOCELLISearch for more papers by this authorM. F. GRENIER-LOUSTALOT, M. F. GRENIER-LOUSTALOTSearch for more papers by this authorP. IRATCABEL, P. IRATCABELSearch for more papers by this author G. BOCELLI, G. BOCELLISearch for more papers by this authorM. F. GRENIER-LOUSTALOT, M. F. GRENIER-LOUSTALOTSearch for more papers by this authorP. IRATCABEL, P. IRATCABELSearch for more papers by this author First published: March 1, 1983 https://doi.org/10.1002/chin.198309072AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume14, Issue9March 1, 1983 RelatedInformation

Stereochemistry of rings. XIII. γ-lactone derivatives: Part 8. The X-ray structure of 3H-5-hydroxyindole

C8H7NO2 (Mr = 149.1) crystallizes in the monoclinic system, space group P21c, with a = 5.836(2), b = 15.164(3), c = 7.507(2) Å, β = 84.2(2)°, V = 660.95(39) Å3, Z = 4 and Dc = 1.50 Mg m−3.The structure has been solved by direct methods and refined to a final R = 0.054 and Rω = 0.047 for 1249 measured reflections. The molecule is planar. The packing is mainly determined by N…O hydrogen bonds.

Stereochemistry of rings. XII. γ-lactone derivatives: Part 7. The X-ray structure of 3-acetylamino-2-thiolanone

C6H9NO2 S(Mr = 159.2) crystallizes in the orthorhombic system, space group. Pna21, with a = 9.423(2), b = 9.115(2), c = 8.965(2) Å, V = 770.0 Å3, Z = 4, Dc = 1.37 g cm−3 and μ(CuKα) = 32.2 cm−1. The structure has been solved by direct methods and refined by full-matrix least-squares to a final R = 0.065 for 1420 observed reflections. The ring is puckered and assumes an envelope conformation. The acetylamino chain occupies a pseudo-equatorial position.

Stereochemistry of rings. IX . γ-Lactone derivatives : Part 5 . The structure of 2-phenoxy-γ-butyrolactone

C 10H 10O 3 crystallises in the monoclinic system, space group P2 1/ n, with a = 19.708(3), b = 7.167(2), c = 6.298(2) Å, β = 84.2(2)°, V= 885.02 Å 3, Z = 4, D c = 1.34 Mg m −3 and μ(Cu- Kα) = 7.81 cm −1. The structure has been solved by direct methods and refined by full-matrix least-squares to R = 0.0528 for 1397 observed reflections. The two mean ring planes form an angle of 132.8° and the lactone ring is in the envelope conformation.