Catalytic asymmetric hetero-Diels–Alder route to a key intermediate for the synthesis of calyxin L |
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Institution: | Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan |
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Abstract: | A catalytic asymmetric formal synthesis of diarylheptanoid natural product calyxin L has been achieved by incorporating an enantio- and diastereoselective hetero-Diels–Alder (HDA) reaction, a Suzuki–Miyaura coupling, and a stereocontrolled catalytic hydrogenation of 2,4,6-trisubstituted dihydropyran as the key steps. The HDA reaction between 4-(4-benzyloxyphenyl)-2-triethylsilyloxy-1,3-butadiene and (4-benzenesulfonyloxyphenyl)propynal catalyzed by dirhodium(II) tetrakis(R)-3-(benzene-fused-phthalimido)-2-piperidinonate], Rh2(R-BPTPI)4, provided cis-2,6-disubstituted tetrahydropyran-4-one in 91% yield with 91% ee. |
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