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

Journal of the American Chemical Society
Sarah E ReismanJohn L Wood

Abstract

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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Citations

Jul 7, 2011·Accounts of Chemical Research·Baomin Wang, Yong Qiang Tu
Aug 20, 2011·Chemical Reviews·Zhen-Lei SongYong-Qiang Tu
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