Enantioselective construction of heterocycles. Synthesis of (R, R)-solenopsin B

DF Taber, PB Deker, HM Fales, TH Jones…

文献索引：Taber, Douglass F.; Deker, P. Bruce Journal of Organic Chemistry, 1988 ,  vol. 53,  # 13  p. 2968 - 2971

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被引用次数: 46

摘要

An enantioselective route to solenopsin B (l), the major saturated component of the alkaloid mixture isolated from the venom of the fire ant, Solenopsis invicta, is reported. The key transformation in this synthesis is the smooth thermolytic cyclization of alkenyl azide 3. The precursor to 3, alcohol 4, is prepared by stereoselective reduction of an enantiomerically pure P-keto ester.