Mitissimolone,a New Sesquiterpene with a Novel Carbon Skeleton from the Basidiomycete Lactarius mitissimus

Mitissimolone, a new regular sesquiterpene possessing a novel carbon skeleton, was isolated from the EtOH extract of fruiting bodies of Lactarius mitissimus. Its structure was determined by extensive spectroscopic analyses including 1D‐ and 2D‐NMR spectra. Mitissimolone inhibited moderately the growth of HeLa cells lines, with an IC₅₀ value of 29.8 μg/ml.     

Phenylglycol Metabolites from Cultures of the Basidiomycete Mycena pruinosoviscida BCC 22723

Mycenadiols A–D ( 1 – 4 , resp.), phenylglycols possessing an ethynyl or vinyl (ethenyl) group were isolated from cultures of the basidiomycete Mycena pruinosoviscida BCC 22723. The structures were elucidated on the basis of NMR‐spectroscopic and mass spectrometric data. The absolute configurations of 1 and 2 were determined by synthesis. Compounds 1 – 4 are synthetically known, but, they have not been previously isolated from natural sources.     

Synthesis and Characterization of New Chalcone Derivatives from cis-Bicyclo[3.2.0]hept-2-en-6-one

A series of chalcone derivatives (3a–k) were prepared via the reaction of cis-bicyclo[3.2.0]hept-2-en-6-one (1) with the respective arylaldehydes (2a–k) and were then characterized by Fourier transform infrared (FT-IR), ¹H NMR, ¹³C NMR, and elemental analyses.     

Two New Sesquiterpene Polyol Esters from Celastrus angulatus

Two novel sesquiterpene polyol esters with a dihydro‐β‐agarofuran (=(3R,5aS,9R,9aS)‐octahydro‐2,2,5a,9‐tetramethyl‐2H‐3,9a‐methano‐1‐benzoxepin) skeleton, (1α,2α,4β,8α,9α)‐1,2,8,12‐tetrakis(acetyloxy)‐9‐(furoyloxy)‐4‐hydroxydihydro‐β‐agarofuran ( 1 ) and (1α,2α,6β,8α,9α)‐1,2,6,8,12‐pentakis(acetyloxy)‐9‐(benzoyloxy)dihydro‐β‐agarofuran ( 2 ), and the three known compounds (1α,2α,4β,6β,8α,9β)‐1,2,6‐tris(acetyloxy)‐9‐(benzoyloxy)‐4‐hydroxy‐8,12‐bis(isobutyryloxy)dihydro‐β‐agarofuran ( 3 ), (1α, 2α,4β,6β,8α,9β)‐1,2,6,8‐tetrakis(acetyloxy)‐9‐(furoyloxy)‐4‐hydroxy‐12‐isobutyryloxy)dihydro‐β‐agarofuran ( 4 ), and (1α,2α,4β,6β,8α,9β)‐1,2,6‐tris(acetyloxy)‐9‐(benzoyloxy)‐4‐hydroxy‐8‐(isobutyryloxy)‐12‐[(2‐methylbutanoyl)oxy]dihydro‐β‐agarofuran ( 5 ) were isolated from the root bark of Celastrus angulatus. Their chemical structures were elucidated by analyses of their MS and NMR data.     

Two New Highly Oxidized Humulane Sesquiterpenes from the Basidiomycete Lactarius mitissimus

Two new highly oxidized humulane sesquiterpenes, mitissimols F ( 1 ) and G ( 2 ), were isolated from the fruiting bodies of Lactarius mitissimus. Their structures were elucidated by using extensive spectroscopic techniques including 1D‐ and 2D‐NMR experiments. The absolute configuration of mitissimol F ( 1 ) was determined by ¹H‐NMR resolution of its diastereoisomeric α‐methoxy‐α‐(trifluoromethyl)benzeneacetates (MTPA). It was shown to be (1S,3E,6S,8R,9R,10S,11R)‐8,9 : 10,11‐diepoxy‐1,6‐dihydroxyhumul‐3‐en‐5‐one (=(1S,2R,4R,6S,8E,11S,12R)‐6,11‐dihydroxy‐1,6,10,10‐tetramethyl‐3,13‐dioxatricyclo[10.1.0.0^2,4]tridec‐8‐en‐7‐one).     

A New Eremophilane Sesquiterpene from Cultures of the Fungus Pholiota nameko

Chemistry of Natural Compounds - A new eremophilane sesquiterpene (1), together with four known sesquiterpenes, donacinol B (2), donacinol C (3), trichapargin A (4), and trichapargin B (5), were...     

Synthesis and Antimicrobial Activity of Some New 5-Arylazothiazole,Pyrazolo[1,5-a] Pyrimidine, [1,2,4]Triazolo[4,3-a]Pyrimidine,and Pyrimido[1,2-a]Benzimidazole Derivatives Containing the Thiazole Moiety

1-(2-(4,5-Dihydro-3-(4-methyl-2-phenylthiazol-5-yl)-5-phenylpyrazol-1-yl)-4-substituted thiazol-5-yl)-2-phenyldiazene were synthesized from hydrazonoyl halides and 3-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-5-phenyl-4,5-dihydro-1H-pyrazole-1-carbothioamide in ethanolic triethylamine. Also, pyrazolo[5,1-a]pyrimidines, 2,3,6-trisubstituted pyridines, and pyrazolo[3,4-d]pyridazines were obtained from sodium salt of 3-hydroxy-1-(4-methyl-2-phenylthiazol-5-yl)prop-2-en-1-one and different heterocyclic amines. All structures of the newly synthesized compounds were elucidated by elemental analysis, spectral data, and alternative synthetic route whenever possible. The newly synthesized compounds were tested towards different microorganisms.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.     

Modified Coumarins. I. Synthesis of 5-Phenyl-7H-furo[2, 3-g]chromen-7-ones and 9-Phenyl-7H-furo-[2, 3-f]chromen-7-ones

5-Phenyl-7H-furo[2,3-g]chromen-7-ones and 9-phenyl-7H-furo-[2,3-f]chromen-7-ones, new analogs of psoralen and allopsoralen, are synthesized from 7-hydroxy- and 5-hydroxy-4-phenylcoumarins     

Two new abietane diterpenes huperphlegmarins A and B from Huperzia phlegmaria

Two new abietane diterpenes, huperphlegmarin A–B (1–2), were isolated from the aerial parts of Huperzia phlegmaria (L.) Rothm. (Lycopodiaceae), in addition to five known compounds including lycoxanthol (3), 21β-hydroxyserrat-14-en-3β-yl acetate (4), 21α-hydroxyserrat-14-en-3β-yl acetate (5), 21α-hydroxyserrat-14-en-3β-ol (6), and fawcettidine (7). Their structures were determined by the combination analyses of spectroscopy, including 1D-, 2D-NMR, HRESIMS, CD and comparison with the reported data in the literature. Huperphlegmarin B (2) presented the rare 1,11-epoxy group in the molecule. Compounds 3, 4, 5 and 6 were performed for AChE inhibitory activity and compound 3 showed the inhibitory activity against AChE with IC₅₀ of 465.6 μg/mL.     

Tridensenal,A Sesquiterpene of Novel Skeleton from the Taiwanese Liverwort Bazzania Tridens

The sesquiterpene aldehyde, tridensenal, of previously unknown skeleton was isolated from the Taiwanese liverwort Bazzania tridens. The structure of tridensenal was elucidated on the basis of spectral data and proved by synthesis of the diastereomeric mixture.     

A novel synthesis of bicyclo[3.3.0]oct-1-en-3-ones from cyclobutanones through [chloro(p-tolylsulfinyl)methylidene]cyclobutanes with ring expansion

Treatment of [chloro(p-tolylsulfinyl)methylidene]cyclobutanes, which were synthesized from cyclobutanones and chloromethyl p-tolyl sulfoxide in three steps in high overall yields, with excess cyanomethyllithium gave enaminonitriles in high yields. Heating of these enaminonitriles with H₃PO₄ in acetic acid gave 2-cyanobicyclo[3.3.0]oct-1-en-3-ones in good yield. On the other hand, treatment of the [chloro(p-tolylsulfinyl)methylidene]cyclobutanes with cyanomethyllithium followed by lithium carbanion of the homologues of acetonitrile afforded enaminonitriles having a substituent at the 3-position. Heating of the enaminonitriles with H₃PO₄ in acetic acid gave 2-substituted bicyclo[3.3.0]oct-1-en-3-ones in good to high yields. This method offers a novel and versatile procedure for synthesis of 2-substituted bicyclo[3.3.0]oct-1-en-3-ones from cyclobutanones in good overall yields.     

A method for synthesis of bicyclo[3.3.0]oct-1-en-3-ones from cyclobutanones with one-carbon ring expansion and its application to a formal synthesis of racemic 1-desoxyhypnophilin

A method for synthesis of 2-cyanobicyclo[3.3.0]oct-1-en-3-ones and 2-substituted bicyclo[3.3.0]oct-1-en-3-ones was developed by assembly of three components, cyclobutanones, chloromethyl p-tolyl sulfoxide, and nitriles, with one-carbon ring expansion of the cyclobutane ring. As an application of this method, a formal synthesis of 1-desoxyhypnophilin in racemic form was performed starting from 3,3-di(phenylthiomethyl)cyclobutanone.     

The dehalogenation of the halo substituted 5H-benzo[a]phenothiazin-5-ones and 3H-phenothiazin-3-ones

6-Bromo- and 6-chloro-5H-benzo[a]phenothiazin-5-ones were dehalinated to 5H-benzo[a]phenothiazin-5-one in the presence of sodium hydrosulfite (disodiumdithionite · 2H₂O) dissolved in aqueous pyridine under nitrogen atmosphere.

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Enthalogenierung von halogensubstituierten 5H-Benzo[a]phenothiazin-5-onen und 3H-Phenothiazin-3-onen

Zusammenfassung 6-Brom- und 6-Chlor-5H-benzo[a]phenothiazin-5-on lassen sich in wäßrigem Pyridin in Gegenwart von Natriumdithionit unter Stickstoff zu 5H-Benzo[a]phenothiazin-3-on enthalogenieren.

     

New efficient synthesis of 2,5,6-trisubstituted oxazolo[5,4-d]pyrimidi-7(6H)-ones via an oxazolyliminophosphorane

A new efficient synthesis of 2,5,6-trisubstituted oxazolo[5,4-d]pyrimidi-7(6H)-ones by consecutive aza-Wittig reaction was developed. The sequential three-component reaction of oxazolyliminophosphorane 4, isocyanates and amines produced 2,5,6-trisubstituted oxazolo[5,4-d]pyrimidi-7(6H)-ones 7 in good overall yields in the presence of catalytic amount of EtONa.     

4-甲氧基-6-甲基-7a-苯基苯并吡喃并[2,3-b]氮丙啶-7-酮的合成及晶体结构研究

通过5-甲基-7-甲氧基异黄酮与盐酸羟胺的缩合制得中间产物4-苯基-5-（2-羟基-4-甲氧基-6-甲基苯基）异恶唑,然后经过光异构化反应合成了4-甲氧基-6-甲基-7a-苯基苯并吡喃并[2,3-b]氮丙啶-7-酮,并采用IR,NMR,HRMS和单晶X-衍射分析对其结构进行了表征.单晶X-衍射分析结果表明：标题化合物属于单斜晶系,空间群P2（1）/n.在其晶体结构中,存在着氢键及芳香堆积作用,这些作用将标题化合物分子组装成了三维网络结构.     

A one-pot [Bmim]OH-mediated synthesis of 3-benzamidocoumarins

The first example of an ionic liquid-promoted one-pot synthesis of 3-benzamidocoumarins from salicylaldehydes and 2-pheny-1,3-oxazolan-5-one via Knoevenagel condensation-ring transformation cascades has been reported. No by-product formation, operational simplicity, ambient temperature and high yield (85-97%) are the salient features of the present synthetic protocol. After isolation of the product, the ionic liquid, [Bmim]OH can be easily recycled for further use without any loss of efficiency.     

A New Jatrophane Diterpenoid Ester from Euphorbia turczaninowii

A new jatrophane diterpenoid ester （2S, 3S, 4R, 5R, 7S, 8R, 13R, 15R） - 3, 5, 7, 8, 15- pentaacetoxy-9, 14-dioxojatropha-6（17）, 11E-diene was isolated from the whole plant of Euphorbia turczaninowii Kar. ＆ Kit.. Its structure was characterized by spectral analysis and confurmed by X-ray crystallographic analysis.     

Simple synthesis of 6-alkyl-5H-benzo[a]phenoxazin-5-ones

6-Alkyl-5H-benzo[a]phenoxazin-5-ones were prepared by the reaction of 5H-benzo[a]phenoxazin-5-one with carboxylic acid in the presence of silver ion and peroxydisulfate.

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Eine einfache Synthese von 6-Alkyl-5H-benzo[a]phenoxazin-5-onen (Kurze Mitteilung)

Zusammenfassung 6-Alkyl-5H-benzo[a]phenoxazin-5-one wurden mittels Reaktion von 5H-Benzo[a]phenoxazin-5-onen mit Carbonsäuren in Gegenwart von Silberionen und Peroxydisulfat dargestellt.