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- Title
Synthesis of Aristotelia-Type Alkaloids. Part VIBiomimetic Synthesis of (+)-Aristofruticosine.
- Authors
Beerli, René; Borschberg, Hans-Jürg
- Abstract
( S)-Perilla alcohol ( 5) was transformed into ( S)-7-(phenylthio)- p-menth-1-en-8-amine ( 11) in five steps. Condensation of this building block with 1-(4-methoxyphenylsulfonyl)-1 H-indole-3-acetaldehyde ( 12) led to the expected imine 15 which cyclized in 54% yield to protected 20-(phenylthio)hobartine 16 upon exposure to anh. HCOOH. Treatment of this intermediate with an alkylating reagent led to (+)-aristofruticosine protected in the indole moiety via an intramolecular, allylic nucleophilic displacement reaction. Subsequent reductive removal of the protecting group completed the first synthesis of the Aristotelia alkaloid (+)-aristofruticosine ((+)- 4). This straightforward synthesis confirmed the tentative structure (+)- 4, proposed by Bick and Hai, and established the hitherto unknown absolute configuration of this metabolite.
- Publication
Helvetica Chimica Acta, 1991, Vol 74, Issue 1, p110
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19910740113