Journal
TETRAHEDRON LETTERS
Volume 56, Issue 11, Pages 1356-1359Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.01.181
Keywords
Eushearilide; Antifungal activity; Total synthesis; Structural determination; Asymmetric synthesis; Lactonization
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Funding
- Ministry of Education, Science, Sports and Culture, Japan
- Center for Chirality
- Grants-in-Aid for Scientific Research [22350044] Funding Source: KAKEN
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An asymmetric total synthesis of the proposed structure of (16Z,20E)-eushearilide, a novel 24-membered macrolide, was achieved via an enantioselective aldol reaction and 2-methyl-6-nitrobenzoic anhydride-mediated macrolactonization. The obtained synthetic compounds were not identical to the natural product. The newly proposed most likely structure of eushearilide, (+/-)-(16E,20E)-eushearilide, was determined on the basis of detailed NMR analysis, and (3R,16E,20E,23R)-(-)-eushearilide was successfully synthesized. A comparison of the optical rotation of (3R,16E,20E,23R)-(-)-eushearilide with that of the natural product confirmed that the true structure of naturally occurring eushearilide is the (3s,16E,20E,23s)-(+)-form. (C) 2015 Elsevier Ltd. All rights reserved.
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