1,721,060 research outputs found

    A Pd-Mediated Approach to the Synthesis of an Unusual beta-Hydroxytryptophan Amino Acid Constituent of Cyclomarin A.

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    A synthetic approach based on a palladium-mediated vinylation of indole derivatives was established for the preparation of 5, a key intermediate in the synthesis of N-(tert-butoxycarbonyl)-L-1H-[(R)-1,1-dimethyl-2,3-epoxypropyl]-beta-hydroxytryptophan ethyl ester (6). Unsatisfying yields were obtained using N-alkyl-3-haloderivatives. The best method proved to be the oxidative coupling on 3-unsubstituted indole derivative

    Microwave accelerated Wittig reactions of stabilized phosphorus ylides with ketones under solvent-free conditions

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    Microwave irradiation accelerates some difficult Wittig reactions of stable phosphorus ylides (e.g. 1) with ketones. Irradiation in a domestic microwave oven of the mixture of reactants, in absence of solvents, allowed to obtain, in shorter times, an improvement of tranformation yields over conventional heating method

    First total synthesis of natural aplyolides B and D, ichthyotoxic macrolides isolated from the skin of the marine mollusk Aplysia depilans

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    A convergent pathway is described for the synthesis of the marine macrolides aplyolides B (2) and D (3). Stereoselective preparation of a key fragment was achieved by Sharpless asymmetric dihydroxylation of eneyne 10

    Potential Alarm Pheromones From the Mediterranean Opisthobranch Scaphander lignarius

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    Two new w-phenyl conjugated trienones, lignarenone-A (2) and lignarenone-B (3), are the main metabolites isolated from the dorsum acetone extract of Scaphander lignarius. Their structures, closely related to 3-methyl navenone-B (1) a minor component of the alarm pheromone mixture of the opisthobranch Navonax inermis, were characterized by spectral methods

    Janolusimide, A Lipophilic Tripeptide Toxin From the Nudibranch Mollusk Janolus-cristatus

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    Tke structure of janolusimide, a lipophilic tripeptide toxic to mice isolated from the nudibranch mollusc Janolus cristatus, has been established by spectroscopic and chemical means

    New Propionate-derived Metabolites From Aglaja-depicta and From Its Prey Bulla-striata (opisthobranch, Mollusks)

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    Two new polypropionate metabolites aglajne-2 (14) and -3 (2) and the previously known aglajne-1 (1) have been isolated from the opisthobranch mollusc Bulla striata, a prey of the opistobranch Aglaja depicta in which these compounds were first detected. This finding establishes the dietary origin of these metabolites in A. depicta. The structures were determined by extensive use of 'H and 13C NMR techniques on the compounds and on their derivatives and by chemical proofs. Two additional compounds (12 and 13), isolated as racemic diastereoisomers, are artifacts originating from aglajne-2 (14) during the extraction and purification procedures. The relative and absolute stereochemistry at C-3 and C-6 of aglajne-1 (1) and -3 (2) has been also determined
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