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

Abstract The first total syntheses of diarylheptanoid natural products (2 R ,4 S ,6 R )-2-(4-hydroxyphenethyl)-6-(4-hydroxyphenyl) tetrahydro-2 H -pyran-4-ol ( 4 ) and (3 R ,5 R )-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.