Synthesis and Mitochondrial Complex I Activity of Annonaceous Trans and Cis Solamins Precursors

Author(s): Julie Defretin, Christophe Gleye, Diego Cortes, Xavier Franck, Reynald Hocquemiller, Bruno Figadere.

Journal Name: Letters in Organic Chemistry

Volume 1 , Issue 4 , 2004

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The efficient synthesis of the common C1-C32 precursor of trans and cis solamins has been achieved with the longest linear sequence of 7 steps from pentadecalactone. The key transformations rely on the iron (III) catalysed Grignard coupling reaction with a vinyl bromide, and the Sharpless asymmetric dihydroxylation. Mitochondrial complex I activity of these annonaceous synthetic precursors highlighted the crucial influence of the terminal butenolide, as well as the tetrahydrofuanic pattern.

Keywords: acetogenins, annonaceae, synthesis, grignard, asymmetric dihydroxylation

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Article Details

Year: 2004
Page: [316 - 322]
Pages: 7
DOI: 10.2174/1570178043400460
Price: $58

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