An 1,2-Elimination Approach to the Enantioselective Synthesis of 1,3-Disubstituted Linear Allenes
作者:Yikang Wu、Yan Zhang、Hong-Dong Hao
DOI:10.1055/s-0029-1219542
日期:2010.4
The construction of 1,3-disubstitutedallene skeleton, which is present in many natural allenes, via an i-PrMgBr-mediated elimination of opticallyactive 3-acetoxy-2-iodo-prop-1-ene derviatives is exemplified through the enantioselective total synthesis of two bioactive natural allenes.
A new synthesis of leukotrieneB3 methyl ester is reported, starting from bis(trimethylsilyl) unsaturated derivatives as building blocks for the triene moiety of the leukotriene. The two stereogenic centers have been generated by enantioselective chemical reduction of two acetylenic ketones with both R- or S-Alpine BoraneR. The three conjugated double bonds system of the leukotriene has been assembled