83 research outputs found

    5-Exo-dig, 5-exo-trig cascade radical cyclisation on sugar-furanose templates: entry to angularly fused oxa-and dioxa-triquinane skeletons

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    Serial radical cyclisation on sugar-furanose templates to create angularly fused oxa- and dioxa-triquinane skeletons has been described, the salient feature of this approach being to incipiently generate a tertiary radical from cyclopropylmethyl bromide with simultaneous release of allyl group and to subsequently incorporate it in the triquinane system

    Ring-closing metathesis mediated total synthesis of microcarpalide and herbarumin III

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    An expedient synthesis of tetrakis (cyclopropylmethyl) methane

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    Synthesis of tetrakis(cyclopropylmethyl)methane, a new symmetric product has been described using the radical mediated gem-diallylation of cyclopropylmethyl xanthate as a key step and its single crystal X-ray analysis established its C2-symmetry

    Carbohydrate-based synthesis of naturally occurring marine metabolites slagenins B and C

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    The first enantioselective syntheses of slagenins B and C, marine metabolites from Agelas nakamurai, starting from L-arabinose have been described

    Stereoselective synthesis of a novel carbocyclic nucleoside

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    Carbohydrate based formal synthesis of stemoamide using ring-closing metathesis

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    A synthesis of stemoamide has been achieved from D-glucose. The stereocontrolled allylation under Barbier reaction conditions led to the installation of the 2-pyrrolidinone ring at C-3 followed by a ring-closing metathesis approach to construct the azepine ring system

    A stereoselective synthesis of the C13-C19 fragment of sanglifehrin A

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    A stereo-controlled radical C-C bond formation involving a 5-chloro-5-deoxy-l-idofurano-6,3-lactone derivative and allyltri-n-butyltin/AIBN is described. Further elaboration led to the synthesis of the C13-C19 segment of sanglifehrin A

    A short and efficient synthetic strategy for the total syntheses of (S)-(+)-and (R)-(−)-plakolide A

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    Concise and efficient total syntheses of anticancer agents (S)-(+)-Plakolide A and (R)-(−)-Plakolide A were accomplished in eight steps and an overall yield of 39% starting from geraniol. The key steps in our strategy are Sharpless asymmetric epoxidation, double elimination, and Stille coupling reactions

    First total synthesis of herbarumin III

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    An asymmetric 10-step total synthesis of herbarumin III in 24% overall yield is described using ring-closing metathesis as the key step

    Towards the enantioselective synthesis of anti-HIV agents litseaverticillols C and K from D-glucose

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    The first enantioselective synthesis towards the litseaverticillols C and K has been achieved, from D-glucose, using the ring closing metathesis (RCM) and Wittig reactions as key steps
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