Peloruside B, A Potent Antitumor Macrolide from the New Zealand Marine Sponge Mycale hentscheli: Isolation, Structure, Total Synthesis, and Bioactivity

摘要

Peloruside B(2), a natural congener of pelorusideA(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 G2/M phase of mitosis similar to paclita xel, and its bioactivity was comparable to that of peloruside A. NMR-directed isolation, structure elucidation, structureconfirmation 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.