Journal
TETRAHEDRON
Volume 70, Issue 24, Pages 3774-3781Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.04.040
Keywords
Topsentolide; Oxylipin; Cytotoxic; Artifact; Marine natural product
Categories
Funding
- MEXT [24658105]
- Grants-in-Aid for Scientific Research [24658105] Funding Source: KAKEN
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The first total synthesis of the marine-derived cytotoxin topsentolide A(2), which eventually culminated in its stereochemical determination, was accomplished in 17 steps from a known chiral alcohol. An improved synthesis of its congener, topsentolide C-2, from a synthetic intermediate of topsentolide A(2) was also performed by utilizing the Yamaguchi lactonization to construct its nine-membered lactone ring. Treatment of epoxide ring-containing topsentolide Ay with HCl/MeOH brought about its quantitative conversion into topsentolide C-2. (C) 2014 Elsevier Ltd. All rights reserved.
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