Shashank N. Mhaldar and Santosh G. Tilve
Org. Biomol. Chem., 2023,21, 5469-5474
DOI:
10.1039/D3OB00707C,
Paper
This article describes an enantioselective strategy for the synthesis of the kainoid component, (+)-allokainic acid using an organocatalytic approach. A cross-aldol reaction catalyzed by diphenylprolinol yielded a highly functionalized γ-lactam with excellent enantio- and diastereoselectivity, and the resulting hydroxy pyrrolidone was then utilized to synthesize Ganem's intermediate of (+)-allokainic acid. Krapcho decarboxylation and Wittig olefination were pivotal transformations towards the final trans-substituted Ganem's intermediate.