Journal of The Chemical Society C: Organic 

About: Journal of The Chemical Society C: Organic is an academic journal. The journal publishes majorly in the area(s): Yield (chemistry) & Ring (chemistry). Over the lifetime, 3897 publications have been published receiving 29608 citations.

Metabolites of Lasiodiplodia theobromae

Abstract: A plant-growth inhibitor produced by Lasiodiplodia theobromae has been shown to be jasmonic acid (Ia). Six other new fungal metabolites have been isolated from L:theobromae—lasiodiplodin (Va), de-O-methyl-lasiodiplodin (Vb), cis-4-hydroxymellein (XIIIa), indole-3-carboxylic acid, 3-formylindole, and ethyl hydrogen fumarate. (–)-Mellein (XIIIb) is also produced.

Unsaturated carbohydrates. Part IX. Synthesis of 2,3-dideoxy-α-D-erythro-hex-2-enopyranosides from tri-O-acetyl-D-glucal

Abstract: Tri-O-acetyl-D-glucal undergoes complete reaction with alcohols in benzene solution in the presence of boron trifluoride to give 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosides. The α-anomers predominate (ca. 90%), and the method can be used to prepare the known crystalline ethyl α-glucoside easily and in greatly improved yield. Other alkyl glycosides have been prepared similarly, and the procedure has afforded means of obtaining the cholesteryl analogue and the disaccharide derivative 6-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose. Tri-O-acetyl-D-glucal again gave the 2,3-unsaturated glycosides on treatment with acetals in the presence of boron trifluoride; no evidence was obtained for the formation of branched-chain products produced by additions to the double bond.

Constitution and biosynthesis of capsaicin

Abstract: Capsaicin, the crystalline pungent principle of Capsicum annuum, has been shown to be a mixture of at least five closely related vanillyl amides. Phenylalanine, various hydroxylated cinnamic acids, and vanillylamine, all labelled with tritium in the aromatic ring, were incorporated biosynthetically into the C6–C1 unit of capsaicin. Tyrosine was incorporated much less efficiently than phenylalanine. The radioactive capsaicin mixture derived biosynthetically from phenylalanine was found to contain most of the activity in the minor, saturated components.

Hydrocarbon constituents of the blue-green algae Nostoc muscorum, Anacystis nidulans, Phormidium luridium and Chlorogloea fritschii

Abstract: The aliphatic hydrocarbon constituents of four blue-green algae, Nostoc muscorum, Anacystis nidulans, Phormidium Iuridium, and Chlorogloea fritschii, have been investigated. The findings indicate that the n-C17 hydrocarbon is the predominant component in the hydrocarbon mixtures. Methyl branchedalkanes seemed to be of particular significance because the methyl branches are not iso- and anteiso-structures. They appear to occur uniquely in blue-green algae and are absent from photosynthetic and non-photosynthetic bacteria. These hydrocarbons have not been found in the green algae, which are more advanced than blue-green algae but are still relatively primitive. Mass spectrometry indicates that the methyl branched alkane from Chlorogloea fritschii may be 4-methylheptadecane. The Nostoc branched C18 compound was studied by i.r., n.m.r., and mass spectrometry. Synthesis of 7,9-dimethylhexadecane and of 7- and 8-methylheptadecanes proved that the branched hydrocarbon consisted of a mixture (1:1) of 7- and 8-methylheptadecanes, which could not be separated by capillary g.l.c.

Heterocyclic rearrangements. Part X. A generalised monocyclic rearrangement

Abstract: A new general class of rearrangements of substituted azoles (III)→(IV) has been recognised, scattered examples from the literature are collated, and further examples described.