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Synthesis of Polycyclic Benzofused Nitrogen Heterocycles via a Tandem Benzannulation/Ring-Closing Metathesis Strategy. Application in a Formal Synthesis of (+)

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  • معلومة اضافية
    • Publisher Information:
      American Chemical Society 2012-03-02T19:16:36Z 2012-03-02T19:16:36Z 2011-02 2011-01
    • نبذة مختصرة :
      A two-stage “tandem strategy” for the synthesis of benzofused nitrogen heterocycles is described that is particularly useful for the construction of systems with a high level of substitution on the benzenoid ring. The first stage in the strategy involves a benzannulation based on the reaction of cyclobutenones with ynamides. This cascade process proceeds via a sequence of four pericyclic reactions and furnishes a multiply substituted aniline derivative which can bear a variety of functionalized substituents at the position ortho to the nitrogen. In the second stage of the tandem strategy, ringclosing metathesis generates the nitrogen heterocyclic ring. This two-step sequence provides efficient access to highly substituted dihydroquinolines, benzazepines, benzazocines, and related benzofused nitrogen heterocyclic systems. The application of this chemistry in a concise formal total synthesis of the anticancer agents (þ)-FR900482 and (þ)-FR66979 is described.
      National Institutes of Health (U.S.) (NIH (GM 28273))
      Merck Research Laboratories
      Boehringer Ingelheim Pharmaceuticals
    • الموضوع:
      Article; http://purl.org/eprint/type/JournalArticle
    • Availability:
      Open access content. Open access content
      Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
    • Note:
      application/pdf
      en_US
    • Other Numbers:
      MYG oai:dspace.mit.edu:1721.1/69574
      0022-3263
      1520-6904
      Mak, Xiao Yin, Aimee L. Crombie, and Rick L. Danheiser. “Synthesis of Polycyclic Benzofused Nitrogen Heterocycles via a Tandem Ynamide Benzannulation/Ring-Closing Metathesis Strategy. Application in a Formal Total Synthesis of (+)-FR900482.” The Journal of Organic Chemistry 76.6 (2011): 1852–1873.
      1141885841
    • Contributing Source:
      MASSACHUSETTS INST OF TECHNOL LIBRS
      From OAIster®, provided by the OCLC Cooperative.
    • الرقم المعرف:
      edsoai.on1141885841
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