Utilization of the Intramolecular Cycloaddition-Cationic π-Cyclization of an Isomünchnone Derivative for the Synthesis of (±)-Lycopodine

…, MA Brodney, JP Marino, SM Sheehan

文献索引：Padwa; Brodney; Marino J.P.; Sheehan Journal of Organic Chemistry, 1997 , vol. 62, # 1 p. 78 - 87

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被引用次数: 106

摘要

A new annulation sequence leading to the tetracyclic skeleton of the Lycopodium family of alkaloids is effected by using the tandem cycloaddition-cationic π-cyclization reaction of an isomünchnone dipole as the key strategic element. Synthesis of the required α-diazo imide precursor involved treating 5-methylcyclohex-2-en-1-one with the organocopper reagent derived from 3-methoxybenzyl chloride in the presence of chlorotrimethylsilane. ...