title: Total synthesis of the potent androgen receptor antagonist (-)-arabilin: a strategic, biomimetic [1,7]-hydrogen shift.
abstract: The first total synthesis of (-)-arabilin, a  Streptomyces  metabolite that inhibits hormone activation of the androgen receptor, has been completed. The key step, a [1,7]-hydrogen shift, establishes the enol ether-containing skipped-tetraene substructure. This nonenzymatic pericyclic reaction is considered to be biomimetic.
authors.affiliation: Department of Chemistry, Stony Brook University, Stony Brook, New York 11794, USA.
authors.forename: Hee Nam
authors.initials: HN
authors.lastname: Lim
authors.forename: Kathlyn A
authors.initials: KA
authors.lastname: Parker
mesh_terms: D000726:Androgen Antagonists / Q000138:chemical synthesis* / Q000494:pharmacology; D032701:Biomimetics; D006859:Hydrogen / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis* / Q000494:pharmacology; D011944:Receptors, Androgen / Q000187:drug effects*
chemical_list: D000726:Androgen Antagonists; D011753:Pyrones; D011944:Receptors, Androgen; C553367:arabilin; D006859:Hydrogen
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