Abstract

Convergent total syntheses of dehydroambliol-A (1a), its unnatural Z isomer 1b, and ambliofuran (2) are described. The syntheses utilized 2-(3'-furyl)-1,3-dithiane (6) as a common intermediate. Analysis of their proton and carbon magnetic resonance spectra confirm that in the natural product dehydroambliol-A and in synthetic dehydroambliol-A the Δ 7 -bond possesses the E geometry, while in the unnatural isomer of dehydroambliol-A, the Δ 7 -bond is of the Z configuration

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