Evolution of a synthetic strategy: total synthesis of (+/-)-welwitindolinone A isonitrile.

نویسندگان

  • Sarah E Reisman
  • Joseph M Ready
  • Matthew M Weiss
  • Atsushi Hasuoka
  • Makoto Hirata
  • Kazuhiko Tamaki
  • Timo V Ovaska
  • Catherine J Smith
  • John L Wood
چکیده

An efficient and highly stereoselective total synthesis of the natural product (+/-)-welwitindolinone A isonitrile (1) is described. The bicyclo[4.2.0]octane core of 1 was established by a regio- and diastereoselective [2+2] ketene cycloaddition. The C12 quaternary center and vicinal stereogenic chlorine were installed in a single operation with excellent stereocontrol via a chloronium ion mediated semipinacol rearrangement. Described strategies for construction of the spiro-oxinole include a SmI2-LiCl mediated reductive cyclization and a novel anionic cyclization that simultaneously constructs the spiro-oxindole and vinyl isonitrile moieties.

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Total synthesis of (+/-)-welwitindolinone a isonitrile.

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عنوان ژورنال:
  • Journal of the American Chemical Society

دوره 130 6  شماره 

صفحات  -

تاریخ انتشار 2008