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Synlett 1999; 1999(4): 429-431
DOI: 10.1055/s-1999-6183
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A Synthesis of Petrofuran Based on the Enantioselective Reduction of 1-Trimethylsilyl-4-alken-1-yn-3-ones

J. Garcia* , M. López, J. Romeu
  • *Departament de Química Orgànica, Universitat de Barcelona, C/Martí i Franquès 1-11, 08028-Barcelona, Catalonia, Spain; Fax +3 49 33 39 78 78; E-mail: jgg@gsaa1.qo.ub.es
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Publication Date:
31 December 1999 (online)

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Highly enantioenriched 4-alken-1-yn-3-ol moiety (1), present in many bioactive acetylenic metabolites from sponges, has been efficiently obtained by reduction of the parent 1-trimethyl-silyl-4-alken-1-yn-3-one (2) with Alpine-Borane or with BH3 · SMe2 in the presence of chiral oxazaborolidines, followed by desilylation of the resulting alcohol. This strategy has been applied to the first stereoselective synthesis of petrofuran 3.

enantioselective reduction - oxazaborolidines - Petrosia sp. - polyacetylenes - sponge metabolites