Spirolaxine and sporotricale: Two long-chain phthalides produced by Sporotrichum laxum

Arnone, Alberto; Assante, Gemma; Nasini, Gianluca; Pava, Orso Vajna de

doi:10.1016/0031-9422(90)85127-2

Cited by 56 publications

(55 citation statements)

References 2 publications

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“…These compounds may belong to the class of undecaketide derivatives such as phanerosporic acid12) and corticiolic acid13). There are many known antibiotics that contain a [5,4]spiroketal, but the presence of a [4,4]spiroketal is rare: some examples are an insect pheromone14'15) and a plant constituent16). We looked for [5,4] …”

Section: Discussionmentioning

confidence: 99%

“…These facts together with the benzene fragment from XHNMRsuppose 3,5-dimethoxyphthalide as a partial structure of 1. Also, the chemical shift of ketal carbon and two oxymethine fragments from XH NMRsuggest the l,6-dioxaspiro [4,4]nonane system. Since the remaining elements are only methylenes with no heteroatom substitution, the whole structure is proposed to be 3,5-dimethoxyphthalide extended with a straight alkyl chain having a 1,6-dioxaspiro- [4,4]nonane system at the end.…”

Section: Producing Strainmentioning

confidence: 92%

“…UVabsorption maxima ofCJ-12,954 at 290.6, 257.6 and 217.4nm are also in good agreement with those of8. Comparisons of 13C NMRdata of the ketal carbon and two oxymethines in spiro-ketal ring should have 7-alkyl-2-methyll ,6-dioxaspiro [4,4]nonane system (around 75, 114 and 80ppm), but not 1,6-dioxaspiro [4,5] …”

Section: Producing Strainmentioning

confidence: 99%

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CJ-12,954 and Its Congeners, New Anti-Helicobacter pylori Compounds Produced by Phanerochaete velutina:Fermentation, Isolation, Structural Elucidation and Biological Activities.

et al. 1997

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Seven new phthalide compoundswith anti-i7elicobacter pylori activities were isolated from the basidiomycete Phanerochaete velutina CL6387, The two most potent phthalide compounds, CJ-12,954 and CJ-13,014, have MICs of 5 ng/ml. The structure-activity relationship shows that the presence of a spiroketal part in addition to the phthalide part, greatly enhances the activity. The phthalide compoundsappear to be specific for H. pylori, since they did not show antibacterial activities when tested against a panel of other microorganisms.Gastric and duodenal ulcers affect a significant portion of the humanpopulation worldwide. Many recent studies have shown a relation between the presence of the

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Section: Discussionmentioning

confidence: 99%

Section: Producing Strainmentioning

confidence: 92%

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CJ-12,954 and Its Congeners, New Anti-Helicobacter pylori Compounds Produced by Phanerochaete velutina:Fermentation, Isolation, Structural Elucidation and Biological Activities.

et al. 1997

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“…The mixture was stirred for 5 min, treated with 3-bromo-1-propene (0.35 g, 2.9 mmol) then heated under reflux for 4 h. The reaction mixture was cooled to room temperature, quenched by the addition water (3 mL) and 1 M HCl (5 mL) then extracted with diethyl ether (25 mL). The organic phase was further washed with water (2 x 10 mL) and brine (10 mL) then dried over MgSO 4 . Evaporation of the solvent in vacuo followed by flash chromatography of the residue using 2% diethyl ether -hexane as eluent afforded the title compound 16 (0.22 g, 67%) as a colourless oil for which the 1H NMR were in agreement with the literature.…”

Section: -(Allyloxy)-3-(trimethylsilyl)prop-2-yne (16)mentioning

confidence: 99%

Synthesis of a spiroacetal intermediate for the synthesis of the anti-Helicobacter pylori agent CJ-12, 954

Brimble¹,

Funnell²,

Gorsuch³

et al. 2001

Arkivoc

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A method has been established for the synthesis of the 5,5-spiroacetal moiety of the antiHelicobacter pylori agents CJ-12,954 1 and CJ-13,014 2 in racemic form and as a mixture of stereoisomers. Retrosynthetically the key spiroacetal 9 is derived from the acyclic protected dihydroxyketone precursor 10 or 11 which in turn are available from enynone 25 or 26. Enynones 25 and 26 were prepared via addition of the acetylide derived from acetylenes 13 or 14 to aldehyde 12 followed by oxidation of the resultant alcohols 23 and 24 respectively. Acetylenes 13 and 14 in turn were available via [2,3]-sigmatropic rearrangement of allyl propargyl ether 16. Extension of this reaction in an asymmetric sense by use of a chiral base would have provided acetylene 14 in enantioenriched form, however, efforts towards this end were disappointing. Enynones 25 and 26 were converted to keto epoxides 10 and 11 respectively by treatment with meta-chloroperbenzoic acid followed by hydrogenation of the acetylene. Attempts to effect deprotection and cyclization of bis-silyl ethers 10 and 11 to spiroacetal 9 were complicated by the presence of the epoxide. In an alternative approach enynone 26 was converted to methyl acetal 29 upon treatment with camphorsulfonic acid in methanol. Subsequent epoxidation of the terminal alkene 29 afforded epoxide 30 which then underwent smooth hydrogenation and cyclization in situ to the desired spiroacetal 9.

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“…Typical examples are are fuscinarin (1) 1 , typhaphthalide (2) 2 , catalpalactone (3) 3 , alcyopterosin E (4) 4 , (+)-spirolaxine (5) 5 , vermistatin (6) 6 , rubiginone-H (7) 7 , (-)-hydrastine (8) 8 , isopestacin (9) 9 , and cryphonectricacid (10) 10 .…”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of Isobenzofuran-1(3h)-Ones Using Sulfuric Acid Immobilized on Silica Under Solvent-Free Conditions and Survey of Third-Order Nonlinear Optical Properties

Maleki

Koushki

Baghayeri

et al. 2015

J. Chil. Chem. Soc.

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Solvent-free synthesis of isobenzofuran-1(3H)-ones have been described via reaction of phthalaldehydic acid (2-carboxybenzaldehyde) with methylaryl or cyclic ketones using sulfuric acid immobilized on silica (H 2 SO 4 -SiO 2 ) in excellent yields (70-88%). The catalyst can be recovered by simple filtration and reused. Also, some of these compounds has been studied the third-order nonlinear optical properties by laser Gaussian z-scan techniques.

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Spirolaxine and sporotricale: Two long-chain phthalides produced by Sporotrichum laxum

Cited by 56 publications

References 2 publications

CJ-12,954 and Its Congeners, New Anti-Helicobacter pylori Compounds Produced by Phanerochaete velutina:Fermentation, Isolation, Structural Elucidation and Biological Activities.

CJ-12,954 and Its Congeners, New Anti-Helicobacter pylori Compounds Produced by Phanerochaete velutina:Fermentation, Isolation, Structural Elucidation and Biological Activities.

Synthesis of a spiroacetal intermediate for the synthesis of the anti-Helicobacter pylori agent CJ-12, 954

One-Pot Synthesis of Isobenzofuran-1(3h)-Ones Using Sulfuric Acid Immobilized on Silica Under Solvent-Free Conditions and Survey of Third-Order Nonlinear Optical Properties

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