Synthesis of the DE-ring of goniodomin A and prediction of its natural relative stereochemistry |
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| Authors: | Takahiro Katagiri Hidetoshi Kawai Takanori Suzuki |
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| Institution: | a Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan
b PRESTO, Japan Science and Technology Agency (JST), 4-1-8 Honcho Kawaguchi, Saitama 332-0012, Japan |
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| Abstract: | Goniodomin A (1) was first isolated from Alexandrium hiranoi as a stereochemically unidentified antifungal agent in 1987 by Murakami. In this study, two stereoisomeric series of non-macrocyclic and macrocyclic DE-ring model compounds of 1 were synthesized, and the natural relative stereochemistry of the DE-ring was predicted by NMR comparison of 1 with these model compounds. |
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| Keywords: | Goniodomin A Polyether macrolide Ireland-Claisen rearrangement NMR analysis Natural product synthesis |
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