title: Peloruside B, a potent antitumor macrolide from the New Zealand marine sponge Mycale hentscheli: isolation, structure, total synthesis, and bioactivity.
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.
authors: Centre for Biodiscovery, Victoria University of Wellington, Wellington, New Zealand.
authors: A Jonathan
authors: AJ
authors: Singh
authors: Chun-Xiao
authors: CX
authors: Xu
authors: Xiaoming
authors: X
authors: Xu
authors: Lyndon M
authors: LM
authors: West
authors: Anja
authors: A
authors: Wilmes
authors: Ariane
authors: A
authors: Chan
authors: Ernest
authors: E
authors: Hamel
authors: John H
authors: JH
authors: Miller
authors: Peter T
authors: PT
authors: Northcote
authors: Arun K
authors: AK
authors: Ghosh
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000302:isolation & purification* / Q000494:pharmacology*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry* / Q000494:pharmacology*; D002453:Cell Cycle / Q000187:drug effects; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009520:New Zealand; D017239:Paclitaxel / Q000737:chemistry / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007783:Lactones; D018942:Macrolides; C414085:peloruside A; C547698:peloruside B; D017239:Paclitaxel