23 research outputs found

    Concise and stereocontrolled synthesis of the southern gamma-butyrolactone subunit of polycavernoside A

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    The southern gamma -butyrolactone subunit 8 of polycavernoside A was readily assembled by a novel and connective methodology involving an initial ene-reaction followed by an intramolecular oxidative cyclisation. (C) 2000 Published by Elsevier Science Ltd

    On the role of triflic acid in the metal triflate-catalysed acylation of alcohols

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    The acylation of alcohols by anhydrides, catalysed by a wide range of metal triflates, is a powerful and mild method for the preparation of a variety of esters. Mechanistic insights demonstrate that triflic acid is generated under these reaction conditions and that, at least, two competing catalytic cycles are operating at the same time: a rapid one involving triflic acid and a slower one involving the metal triflate. (C) 2003 Elsevier Ltd. All rights reserved

    Efficient and connective synthesis of substituted butyrolactones and exo-methylene butyrolactones

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    A variety of alpha-(trimethylsilylmethyl)- substituted butyrolactones are readily accessed by a novel tandem ene-reaction/oxidative desilylation of a range of aldehydes, Subsequent functionalisation led to an efficient methodology for the preparation of exo-methylene butyrolactones. (C) 2000 Published by Elsevier Science Ltd

    Tandem ene-reaction/intramolecular Sakurai Cyclisation (IMSC): A novel access to polysubstituted tetrahydropyrans and gamma-butyrolactones using a unique allylation strategy

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    The ene-reaction between a variety of aldehydes and allylsilane 22 generates highly functionalised homoallylic alcohols 23. These adducts undergo a subsequent Intramolecular Sakurai Cyclisation (IMSC), affording in good yields polysubstituted tetrahydropyran derivatives. Furthermore, oxidative desilylation of 23 provides an efficient, connective access to a range of gamma-butyrolactones and alpha-methylene-gamma-butyrolactones

    Neutral, non-racemising, catalytic aerobic oxidation of alcohols

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    A novel procedure for the catalytic aerobic oxidation of alcohols into carbonyl derivatives under neutral, non-racemising conditions, is reported. (C) 2001 Elsevier Science B.V. All rights reserved

    Using toluates as simple and versatile radical precursors

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    The electrolysis of toluate esters leads smoothly to the formation of the radical of the alkyl fragment. This property has been used to develop a new electrochemical deoxygenation reaction
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