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Updated: Jan 5, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Total Synthesis and Stereochemical Revision of Biemamides B and D
Nikhil Srivastava1, Lingamurthy Macha1, Hyun-Joon Ha1
1Department of Chemistry , Hankuk University of Foreign Studies , Yongin 17035 , Korea.
Abstract:
The first expedient asymmetric synthesis of both enantiomers of 5,6-dihydrouracil-type marine natural products biemamides B and D was achieved from chiral 1-(α-methylbenzyl)aziridine-2-carboxylate. The key steps involved in the synthetic route are regio- and stereoselective aziridine ring opening via azide followed by a base-induced cyclization reaction. After comparison of ECD and optical rotation data of both synthetic enantiomers, the absolute configuration of natural biemamides B and D at the C5 position has been assigned as (-)-(5S), which is an enantiomer to the originally proposed structure (-)-(5R).
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