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Synthesis of Farnesol Analogues Containing Triazoles in Place of Isoprenes through 'Click Chemistry'

ABSTRACT: A solid-phase three-component Huisgen reaction has been used to generate polar farnesol and farnesyl diphosphate analogues. The Cu(I)-catalyzed 1,3-cycloadditions of various azides with solid supported (E)-3-methylhept-2-en-6-yn-1-ol provided only the 1,4-disubstituted 1,2,3-triazole regioisomers. The organic azides were generated in situ to minimize handling of potentially explosive azides. We have employed this powerful 'click chemistry' to make farnesol analogues where both ?- and ?-isoprenes were replaced by triazole and substituted aromatic rings, respectively.

SUBMITTER: Subramanian T 

PROVIDER: S-EPMC3485679 | biostudies-literature | 2012 Oct

REPOSITORIES: biostudies-literature

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Synthesis of Farnesol Analogues Containing Triazoles in Place of Isoprenes through 'Click Chemistry'

Subramanian Thangaiah T   Parkin Sean S   Spielmann H Peter HP  

Synlett : accounts and rapid communications in synthetic organic chemistry 20121001 17

A solid-phase three-component Huisgen reaction has been used to generate polar farnesol and farnesyl diphosphate analogues. The Cu(I)-catalyzed 1,3-cycloadditions of various azides with solid supported (E)-3-methylhept-2-en-6-yn-1-ol provided only the 1,4-disubstituted 1,2,3-triazole regioisomers. The organic azides were generated in situ to minimize handling of potentially explosive azides. We have employed this powerful 'click chemistry' to make farnesol analogues where both β- and γ-isoprenes  ...[more]

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