A two-step synthesis of marine origin brominated alkaloids wilsoniamines A (1) and B (2), isolated from Australian bryozoan Amathia wilsoni Kirkpatrick, possessing a novel hexahydro-1H-pyrrolo[1,2-c]imidazol-1-one ring system is described. The core hexahydro-1H-pyrrolo[1,2-c]imidazol-1-one ring systems is constructed through a condensation reaction between (2,4,6-tribromo-3- methoxyphenyl)acetaldehyde and (S)-N-methylpyrrolidine-2-carboxamide as key steps. The orientation of substituted benzyl side-chain in the two epimeric natural products was controlled by carrying out the key condensation reaction under kinetic or thermodynamic conditions. © 2013 Elsevier Ltd. All rights reserved.

Faiz Ahmed Khan

Department of Chemistry

S. Ahmad

Indian Institute of Technology Hyderabad (IITH) is a premier institute of science and technology established in 2008. IITH has been consistently ranked in the&nbsp;<a href="https://iith.ac.in/reports/" rel="noopener noreferrer">top 10 institutes</a>&nbsp;in India for Engineering&nbsp;<a href="https://www.nirfindia.org/2021/EngineeringRanking.html" rel="noopener noreferrer" target="_blank">according to NIRF</a>&nbsp;making it one of the most coveted schools for science and technology in the country.

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Journal	Tetrahedron Letters
ISSN	00404039