School of Chemical Sciences, Goa University, Taleigao Plateau, Goa, 403206, India.
Department of Chemistry, Dhempe College of Arts & Science, Miramar, Goa, 403001, India.
Org Biomol Chem. 2023 Jul 5;21(26):5469-5474. doi: 10.1039/d3ob00707c.
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 -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 -substituted Ganem's intermediate.
本文描述了一种使用有机催化方法合成 kainoid 成分(+) - 别构氨酸的对映选择性策略。二苯脯氨醇催化的交叉醛醇反应生成了具有优异对映选择性和非对映选择性的高官能化 - 内酰胺，所得的羟基吡咯烷酮随后用于合成(+) - 别构氨酸的 Ganem 中间体。Krapcho 脱羧和Wittig 烯烃化为最终取代 Ganem 中间体的关键转化。
