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Synfacts 2008(6): 0558-0558  
DOI: 10.1055/s-2008-1072608
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Papaverine

Contributor(s): Philip Kocienski
C. D. Gilmore, K. M. Allan, B. M. Stoltz*
California Institute of Technology, Pasadena, USA
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Publication History

Publication Date:
21 May 2008 (online)

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Significance

Orthogonal modes of reactivity are displayed by differently substituted N-acyl en­amine derivatives in the presence of arynes. Simple N-acyl derivatives react at carbon to give isoquinolines as illustrated by the synthesis of the opiate alkaloid papaverine shown below. On the other hand, N-Boc-dehydroamino acids react at nitrogen to give indolines.