TY - JOUR
T1 - Synthesis of farnesol analogues containing triazoles in place of isoprenes through 'click chemistry'
AU - Subramanian, Thangaiah
AU - Parkin, Sean
AU - Spielmann, H. Peter
PY - 2012
Y1 - 2012
N2 - 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 were replaced by triazole and substituted aromatic rings, respectively.
AB - 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 were replaced by triazole and substituted aromatic rings, respectively.
KW - cancer
KW - click chemistry
KW - cycloaddition
KW - farnesol
KW - farnesyldiphosphate
KW - solid-phase synthesis
KW - triazoles
UR - http://www.scopus.com/inward/record.url?scp=84866644783&partnerID=8YFLogxK
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U2 - 10.1055/s-0031-1290461
DO - 10.1055/s-0031-1290461
M3 - Article
AN - SCOPUS:84866644783
SN - 0936-5214
VL - 23
SP - 2539
EP - 2543
JO - Synlett
JF - Synlett
IS - 17
ER -
