Asymmetric Total Syntheses of the trans-2-Aryl-6-alkyltetrahydropyrans Diospongin B and Parvistones D and E from a Common Precursor

Abstract

Asymmetric total syntheses of diospongin B and parvistones D and E are reported. Our strategy features a high-yielding three-step reaction sequence: Achmatowicz rearrangement, reductive γ-deoxygenation, and Matsuda–Heck coupling to construct the rare and challenging trans-2-aryl-6-alkyltetrahydropyrans, which serve as common intermediates for the syntheses of diospongin B, and parvistones D and E.

Key words

diospongin B - parvistone E - trans-tetrahydropyran - Achmatowicz rearrangement - 9-deoxygoniopypyrone - 8-epi-9-deoxygoniopypyrone

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