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Updated: Jun 3, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Asymmetric Total Syntheses of Sarglamides A, C, and E
Xinyu Wang1, Yunxia Yang1, Jing Fang1
1State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000 Gansu, P. R. China.
Abstract:
The asymmetric total syntheses of sarglamides A, C, and E in concise and protecting group free fashion is disclosed. Key steps involve an endo-selective Diels-Alder reaction to construct the bicyclo[2.2.2]nonane framework, a nucleophilic addition and an intramolecular aza-Michael addition to install the pyrrolidine ring, and a final cinnamoylation reaction. Sarglamide C is biomimetically transformed into E through a Brønsted acid mediated oxy-cyclization. Sarglamide D is also accessible from C based on Yue's research. This work provides an efficient asymmetric approach to the syntheses of sarglamides and also provides insights into understand the plausible biogenetic pathway of these monoterpenoid-indolidinoid hybrid structures.
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