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: Beta-lactones as synthetic vehicles in natural product synthesis
    sub title: total syntheses of schulzeines B & C and omphadiol, and studies toward the total syntheses of scabrolides A & B and sinulochmodin C
  name:
    name part: Liu, Gang.
    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: 2012
    issuance: monographic
  language:
    language term: eng
  physical description:
    form: remote
    extent: 1 online resource.
  abstract: β-Lactones are a class of structurally unique compounds. The versatile reactivity patterns offered by β-lactones have enable chemists to utilize them as powerful synthetic vehicles in complex molecule synthesis. In the total syntheses of the naturally occurring, α-glucosidase inhibitors schulzeines B & C, a readily available trichloromethyl β-lactone was used as a versatile masked surrogate for bishomoserine aldehyde, which led to a highly efficient construction of the core structures through a pivotal Pictet-Spengler condensation and a Corey-Link reaction. The first total synthesis of (+)-omphadiol was achieved in ten steps from (R)-carvone. This synthesis features a three-step synthesis of a bicyclic β-lactone, which constitutes the key intermediate for the highly stereocontrolled introduction of the six contiguous stereogenic centers in the natural product. In efforts toward the total syntheses of scabrolides A & B and sinulochmodin C via transannular C-H insertions, β-lactones served as the key intermediates for the synthesis of complex macrocyclic model substrates. These model studies provided valuable insights into the reactivity and selectivity issues for transannular C-H insertion reactions.
  note: by Gang Liu.
  note: "Major Subject: Chemistry"
  note: Electronic resource.
  note: Doctor of Philosophy Texas A&M University 2011 http://hdl.handle.net/1969.1/ETD-TAMU-2011-12-10494
  note: Includes bibliographical references.
  note: Text (Dissertation)
  subject:
    topic: Major Chemistry
  subject:
    topic: omphadiol
  subject:
    topic: β-Lactones
  subject:
    topic: schulzeines
  subject:
    topic: scabrolides
  subject:
    topic: total synthesis
  subject:
    topic: sinulochmodin C
  identifier: http://hdl.handle.net/1969.1/ETD-TAMU-2011-12-10494
  record info:
    record content source: TXA
    record creation date: 121008
    record change date: 20150922122009.0
    record identifier: in00002773813