Cycloaddition reactions of imines with 3-thiosuccinic anhydrides: Synthesis of the tricyclic core of martinellic acid
2006
Arylthio-substituted succinic anhydrides undergo cycloaddition reactions with imines to produce γ-lactams in high yield and with high diastereoselectivity. The origin of the selectivity is proposed to result from anion−π repulsion in the transition state. The utility of this technique is demonstrated in a synthesis of the carbon framework common to the alkaloids martinellic acid and martinelline in five steps.
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