rdf-syntax-grammar
mods:
  schema location: http://www.loc.gov/mods/v3 http://www.loc.gov/standards/mods/v3/mods-3-2.xsd
  title info:
    title: Synthetic studies toward palau'amine and enantioselective total synthesis of biogenetically related (+)-phakellin and (+)-monobromophakellin
  name:
    name part: Wang, Shaohui.
    role:
      role term: creator
  name:
    name part: Romo, Daniel
    role:
      role term: thesis advisor.
  type of resource: text
  genre: bibliography
  origin info:
    place:
      place term: txu
    date issued: 2010
    issuance: monographic
  language:
    language term: eng
  physical description:
    form: electronic
    form: remote
    extent: 1 online resource.
  abstract: Oroidin alkaloids, also known as pyrrole-imidazole alkaloids, have become a hot area of chemical and biological research due to their diverse and intriguing structural features and biological activities. Palau'amine (i), one of the hexacyclic oroidin-derived secondary metabolites, contains a fully substituted chloro-cyclopentane ring, a piperazinone moiety and two cyclic guanidines. With the uniqueness and complexity of its structure, palau'amine has been a synthetic challenge and has not yet succumbed to total synthesis. The overall objective of this work was to explore synthetic pathways toward palau'amine and biogenetically related congeners. Most of the work was focused on developing a synthetic pathway for the palau'amine structure proposed in its isolation report dated back to 1993. Starting from a Diels-Alder adduct (iii), oxidation/chlorination followed by phakellin (ii) annulation afforded an advanced pentacyclic intermediate possessing all the carbon framework and all but one ring system of palau'amine. Recently, however, a series of reports questioned the originally proposed palau'amine structure and called for a revision of the stereochemistry of two carbon centers (iv). Now palau'amine has an identical chlorocyclopentane core with axinellamine (vi). With the target changed, we devised a new biomimetic pathway toward both natural products via a common intermediate (v), which was synthesized in 12 steps from the Diels-Alder adduct (iii).
  note: by Shaohui Wang.
  note: "Major Subject: Chemistry"
  note: Title from author supplied metadata (automated record created 2010-03-12 12:08:51).
  note: Electronic resource.
  note: Doctor of Philosophy Texas A&M University 2008 http://hdl.handle.net/1969.1/ETD-TAMU-2680
  note: Includes bibliographical references.
  note: Text (Dissertation)
  subject:
    topic: Major chemistry
  subject:
    topic: Phakellin
  subject:
    topic: Palau'amine
  subject:
    topic: Synthesis
  subject:
    topic: Alkaloid
  identifier: http://hdl.handle.net/1969.1/ETD-TAMU-2680
  record info:
    record content source: TXA
    record creation date: 100429
    record change date: 20151201150201.0
    record identifier: in00002555673