Total Synthesis of the Spirocyclic Oxindole Alkaloids Corynoxine, Corynoxine B, Corynoxeine, and Rhynchophylline

…, JH van Maarseveen, H Hiemstra

文献索引：Wanner, Martin J.; Ingemann, Steen; Van Maarseveen, Jan H.; Hiemstra, Henk European Journal of Organic Chemistry, 2013 , # 6 p. 1100 - 1106

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被引用次数: 6

摘要

Abstract Racemic total syntheses of four spirocyclic oxindole alkaloids are reported. The general starting material was an N-2-butenylated 2-hydroxytryptamine, which underwent a base-mediated Mannich spirocyclisation with a functionalised aldehyde to generate the C- ring. The second key step was a Pd-catalysed cyclisation of an α-keto ester enolate (in the original aldehyde) onto an allylic carbonate (in the N-substituent) to form the D-ring. The ...