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Synfacts 2006(7): 0642-0642  
DOI: 10.1055/s-2006-941823
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (±)-Welwitindolinone A Isonitrile

Contributor(s): Philip Kocienski, Thomas Snaddon
S. E. Reisman, J. M. Ready, A. Hasuoka, C. J. Smith, J. L. Wood*
Yale University, New Haven, USA
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Publication History

Publication Date:
22 June 2006 (online)

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Significance

Welwitindolinone A isonitrile displays potent antifungal activity. Noteworthy features of this synthesis include (a) the use of a chloronium ion induced semi-pinacol rearrangement to install the C12 and C13 stereocenters (C → E) and (b) the conversion of F into Welwitindolinone A isonitrile via a novel spiro-oxindole-forming reaction. For an alternative synthesis of Welwitindolinone A isonitrile, see: P. S. Baran, J. M. Richter J. Am. Chem. Soc. 2005, 127, 15394-15396.