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

  1. Author:
    Singh, A. J.
    Xu, C. X.
    Xu, X. M.
    West, L. M.
    Wilmes, A.
    Chan, A.
    Hamel, E.
    Miller, J. H.
    Northcote, P. T.
    Ghosh, A. K.

  2. Author Address

    [Singh, A. Jonathan; Wilmes, Anja; Chan, Ariane; Miller, John H.; Northcote, Peter T.] Victoria Univ Wellington, Ctr Biodiscovery, Wellington, New Zealand. [Xu, Chun-Xiao; Xu, Xiaoming; Ghosh, Arun K.] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA. [Xu, Chun-Xiao; Xu, Xiaoming; Ghosh, Arun K.] Purdue Univ, Dept Med Chem, W Lafayette, IN 47907 USA. [Hamel, Ernest] NCI, Toxicol & Pharmacol Branch, Dev Therapeut Program, Div Canc Treatment & Diag,NIH, Frederick, MD 21702 USA. [West, Lyndon M.] Florida Atlantic Univ, Dept Chem & Biochem, Boca Raton, FL 33431 USA.;Northcote, PT, Victoria Univ Wellington, Ctr Biodiscovery, Wellington, New Zealand.;peter.northcote@vuw.ac.nz akghosh@purdue.edu
    1. Year: 2010
    2. Date: Jan
  2. Journal: Journal of Organic Chemistry
    1. 75
    2. 1
    3. Pages: 2-10
  4. Type of Article: Article
  5. ISSN: 0022-3263
  1. Abstract:

    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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External Sources

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  2. DOI: 10.1021/jo9021265
  3. View record in Web of Science®
  4. WOS: 000273013000002

Library Notes

  1. Fiscal Year: FY2009-2010
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