Stereoselective Total Synthesis of Bioactive Styryllactones: 9-Deoxygoniopypyrone, Goniopypyrone and 7-epi-Goniofufurone

Abstract

Stereoselective synthesis of the bioactive styryllactones (+)-9-deoxygoniopypyrone, (+)-goniopypyrone and (+)-7-epi-goniofufurone has been achieved from d-(-)-tartaric acid. The key step involves the elaboration of a trihydroxy ester to the title compounds utilizing high-yielding stereoselective transformations.

Key words

styryllactone - goniopypyrone - 7-epi-goniofufurone - tartaric acid

References

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7

The diastereomeric ratio (5:1) of the formed alcohols was estimated by ¹H NMR spectroscopy. The stereochemistry of the alcohols was further corroborated by conversion into the natural product. Following a sequence that is outlined for goniopypyrone, the major product obtained in the addition of vinylmagnesium bromide to aldehyde 17 was converted into 9-epi-goniopypyrone in 10.5% overall yield starting from trihydroxy ester (Scheme [6] ).

Scheme 6