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Total Syntheses of (-)-Mesembrane and (-)-Mesembrine via Palladium-Catalyzed Enantioselective Allylic Substitution and Zirconium-Promoted Cyclization

M Mori, S Kuroda, CS Zhang, Y Sato

文献索引:Mori; Kuroda; Zhang; Sato Journal of Organic Chemistry, 1997 , vol. 62, # 10 p. 3263 - 3270

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被引用次数: 85

摘要

4-Arylhexahydroindole derivatives 5 were synthesized from 2-arylcyclohexenyl allylamine derivatives 4, which have a large protecting group on nitrogen, using zirconium-promoted cyclization. Reaction of 4e with Cp2ZrBu2, followed by treatment with MeMgBr and then O2, gave 2a in 63% yield by a one-pot reaction, since the approach of O2 to zirconium was prevented by the aryl group. The total syntheses of (±)-mesembrane and (±)-mesembrine ...