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Synthesis 1997; 1997(1): 107-112
DOI: 10.1055/s-1997-1492
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The Total Synthesis of (+)-Petasin and (+)-Isopetasin

Matthias C. Witschel, Hans Jürgen Bestmann*
  • *Institut für Organische Chemie II der Universität Erlangen-Nürnberg, Henkestr. 42, D-91054 Erlangen, Germany, Fax +49(9131)856864
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Publication Date:
31 December 2000 (online)

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Petasin 1 and isopetasin 2, anti-inflammatory and analgesic components of the butterbur (Petasites hybridus), were prepared for the first time in a short and enantioselective synthesis. The key steps were a Michael addition/alkylation (78), an enamine alkylation to give 9 and a cyclization with N-phenyliminoketenylidenetriphenylphosphorane 11 (1015).

petasin - isopetasin - isopetasol - cumulated ylides - intramolecular Wittig reaction