期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 75, 期 1, 页码 2-10出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo9021265
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资金
- National Institutes of Health and Purdue University
- NZ Foundation for Research, Science & Technology (FRST)
- Cancer Society of New Zealand
- Curtis-Gordon Research Scholarship in Chemistry
- Wellington Medical Research Foundation
- NZ Genesis Oncology
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM053386, R37GM053386] Funding Source: NIH RePORTER
Peloruside B (2), a natural congener of peloruside A (1), was isolated in sub-milligram quantities from the New Zealand marine sponge Mycale hentscheli. Peloruside B promotes microtubule polymerization and arrests cells in the G(2)/M phase of mitosis similar to paclitaxel, and its bioactivity was comparable to that of peloruside A. NMR-directed isolation, structure elucidation, structure confirmation by total synthesis, and bioactivity of peloruside B are described in this article. The synthesis features Sharpless dihydroxylation, Brown's asymmetric allylboration reaction, reductive aldol coupling, Yamaguchi macrolactonization, and selective methylation.
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