Stereoselective Synthesis of 2,2,6,6-Tetrasubstituted Tetrahydropyrans

Abstract

A new entry to the synthesis of 3-hydroxy-2,2,6,6-tetrasubstituted tetrahydropyrans has been achieved, avoiding problems encountered in the use of double bond assisted endo-tet cyclization reactions. These compounds are precursors of β-pyrones present in antiviral compounds.

Key words

tetrahydropyrans - iodoetherification - stereoselectivity - cyclizations

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24

Crystal data for 23a: C₉H₁₈O₅, M = 174.23, monoclinic, space group C2, a = 10.971(2), b = 5.711(7), c = 16.242(2)Å, β = 105.63(1)°, V = 980.0(2)ų, Z = 4, D _c = 1.181 g cm^-3, µ(Cu-K_α) = 7.07 cm^-1, F(000) = 384. Data for compound 23a, 924 independent reflections, 2θ < 64.96°, were measured on a Seifert XRD 3000 rotating anode diffractometer with Cu-K_α radiation (graphite monochromator) using ω-scans. The structures were solved by direct methods and the non-hydrogen atoms were refined anisotropically by full-matrix least squares based on F ² to give R1 = 0.0497 and wR2 = 0.1162 for 924 independent observed reflections [|F_o| > 4σ(|F_o|)]