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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
34
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pubmed:dateCreated |
2008-12-2
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pubmed:abstractText |
We describe in full the first synthesis of the potent insect antifeedant azadirachtin through a highly convergent approach. An O-alkylation reaction is used to unite decalin ketone and propargylic mesylate fragments, after which a Claisen rearrangement constructs the central C8-C14 bond in a stereoselective fashion. The allene which results from this sequence then enables a second critical carbon-carbon bond forming event whereby the [3.2.1] bicyclic system, present in the natural product, is generated via a 5-exo-radical cyclisation process. Finally, using knowledge gained through our early studies into the reactivity of the natural product, a series of carefully designed steps completes the synthesis of this challenging molecule.
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
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pubmed:status |
MEDLINE
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pubmed:issn |
1521-3765
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pubmed:author |
pubmed-author:Abad-SomovillaAntonioA,
pubmed-author:AndersonJames CJC,
pubmed-author:AyatsCarlesC,
pubmed-author:BänteliRolfR,
pubmed-author:BeckmannEdithE,
pubmed-author:BoyerAlistairA,
pubmed-author:BrascaMaria GMG,
pubmed-author:BroughtonHoward BHB,
pubmed-author:BurkeBrenda JBJ,
pubmed-author:CleatorEdE,
pubmed-author:CraigDonaldD,
pubmed-author:DenholmAlastair AAA,
pubmed-author:DentonRoss MRM,
pubmed-author:Durand-RevilleThomasT,
pubmed-author:GöbelMichaelM,
pubmed-author:GobbiLuca BLB,
pubmed-author:GrayBrian LawrenceBL,
pubmed-author:GutteridgeClaire ECE,
pubmed-author:HahnNorbertN,
pubmed-author:HardingSarah LSL,
pubmed-author:JennensDavid CDC,
pubmed-author:JennensLynnL,
pubmed-author:KolbHartmuth CHC,
pubmed-author:KootWin-JanWJ,
pubmed-author:LeySteven VSV,
pubmed-author:LovellHelen JHJ,
pubmed-author:LovellPeter JPJ,
pubmed-author:MaslenSarah LSL,
pubmed-author:MattesAmosA,
pubmed-author:McCuskerCatherine FCF,
pubmed-author:PapeAndrew RAR,
pubmed-author:PintoAndreaA,
pubmed-author:SantafianosDinosD,
pubmed-author:ScottJames SJS,
pubmed-author:ShenShui-JieSJ,
pubmed-author:ShinJun-JaeJJ,
pubmed-author:SmithStephen CSC,
pubmed-author:SomersAndrew QAQ,
pubmed-author:SpillingChristopher DCD,
pubmed-author:StelzerFrankF,
pubmed-author:ToogoodPeter LPL,
pubmed-author:TurnerRichard MRM,
pubmed-author:VeitchGemma EGE,
pubmed-author:WoodAnthonyA,
pubmed-author:ZumbrunnCorneliaC,
pubmed-author:de la PuenteMary LML
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pubmed:issnType |
Electronic
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pubmed:volume |
14
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
10683-704
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pubmed:dateRevised |
2009-8-4
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pubmed:meshHeading |
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pubmed:year |
2008
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pubmed:articleTitle |
The synthesis of azadirachtin: a potent insect antifeedant.
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pubmed:affiliation |
Department of Chemistry, University of Cambridge, UK. svl1000@cam.ac.uk
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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