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Total Synthesis and Structural Revision of Mangrolide D
Hiromu Hattori1, Lukas V Hoff1, Karl Gademann1
1Department of Chemistry , University of Zurich , Winterthurerstrasse 190 , CH-8057 Zurich , Switzerland.
Abstract:
The unique 18-membered macrocyclic natural product mangrolide D was prepared in totally synthetic form. Key steps feature an Au-catalyzed glycosylation, aza-Michael addition, and LaLi3tris(binaphthoxide) catalyzed epoxidation. Detailed analysis of the constitution and configuration of the carbohydrate segment and the total synthesis of the revised structure led to structural revision of the originally proposed structure.
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