title: Enantioselective divergent syntheses of several polyhalogenated Plocamium monoterpenes and evaluation of their selectivity for solid tumors.
abstract: The family of polyhalogenated monoterpenes from Plocamium counts over a hundred known members. Using glyceraldehyde acetonide as a chiral-pool precursor, an enantioselective and divergent strategy was developed that provides a blueprint for the synthesis of many of the small yet complex acyclic members of this family. The broad applicability of this approach is demonstrated with the short, eight-step synthesis of four natural products and three analogues. These syntheses are the first of any members of the acyclic polyhalogenated Plocamium monoterpenes and permitted the evaluation of their selectivity against a range of tumor cell lines.
authors.affiliation: 1102 Natural Sciences II, Department of Chemistry, University of California, Irvine, Irvine, CA 92697 (USA).
authors.forename: Carl V
authors.initials: CV
authors.lastname: Vogel
authors.forename: Halina
authors.initials: H
authors.lastname: Pietraszkiewicz
authors.forename: Omar M
authors.initials: OM
authors.lastname: Sabry
authors.forename: William H
authors.initials: WH
authors.lastname: Gerwick
authors.forename: Frederick A
authors.initials: FA
authors.lastname: Valeriote
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Vanderwal
mesh_terms: D045325:HCT116 Cells; D006801:Humans; D039821:Monoterpenes / Q000138:chemical synthesis* / Q000627:therapeutic use; D009369:Neoplasms / Q000188:drug therapy*; D044725:Plocamium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D039821:Monoterpenes
keywords: antitumor agents; chlorination; olefination; stereocontrol; total synthesis