Enantioselective syntheses of diarylheptanoids (2R,4S,6R)-2-(4-hydroxyphenethyl)-6-(4-hydroxyphenyl) tetrahydro-2H-pyran-4-ol and (3R,5R)-1,7-bis(4-hydroxyphenyl)heptane-3,5-diol

Yadav, Jhillu Singh ; Gyanchander, Eppa ; Bujaranipalli, Sheshurao ; Das, Saibal (2015) Enantioselective syntheses of diarylheptanoids (2R,4S,6R)-2-(4-hydroxyphenethyl)-6-(4-hydroxyphenyl) tetrahydro-2H-pyran-4-ol and (3R,5R)-1,7-bis(4-hydroxyphenyl)heptane-3,5-diol Tetrahedron Letters, 56 (11). pp. 1360-1362. ISSN 0040-4039

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Official URL: http://doi.org/10.1016/J.Tetlet.2014.12.144

Related URL: http://dx.doi.org/10.1016/J.Tetlet.2014.12.144

Abstract

The first total syntheses of diarylheptanoid natural products (2R,4S,6R)-2-(4-hydroxyphenethyl)-6-(4-hydroxyphenyl) tetrahydro-2H-pyran-4-ol (4) and (3R,5R)-1,7-bis (4-hydroxyphenyl)heptane-3,5-diol (12) were accomplished using substrate selective hydrogenation, ring cleavage of tetrahydropyran ring, and Keck–Maruoka allylation as the key synthetic steps.

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