688004-85-5Relevant articles and documents
Evolution of a synthetic strategy: Total synthesis of (±)- welwitindolinone A isonitrile
Reisman, Sarah E.,Ready, Joseph M.,Weiss, Matthew M.,Hasuoka, Atsushi,Hirata, Makoto,Tamaki, Kazuhiko,Ovaska, Timo V.,Smith, Catherine J.,Wood, John L.
, p. 2087 - 2100 (2008)
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 Sml 2-LiCl mediated reductive cyclization and a novel anionic cyclization that simultaneously constructs the spiro-oxindole and vinyl isonitrile moieties.
