Subramanian Thangaiah, Parkin Sean, Spielmann H Peter
Department of Cellular and Molecular Biochemistry, University of Kentucky, Lexington, KY, 40536, USA.
Synlett. 2012 Oct;23(17):2539-2543. doi: 10.1055/s-0031-1290461.
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.
一种固-相三组分惠斯根反应已被用于生成极性法尼醇和法尼基二磷酸类似物。各种叠氮化物与固相负载的（E）-3-甲基庚-2-烯-6-炔-1-醇在铜（I）催化下的1,3-环加成反应仅生成1,4-二取代的1,2,3-三唑区域异构体。有机叠氮化物原位生成，以尽量减少对潜在爆炸性叠氮化物的处理。我们已采用这种强大的“点击化学”方法来制备法尼醇类似物，其中β-异戊二烯和γ-异戊二烯分别被三唑和取代的芳环取代。
