Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 1, Pages 644-651Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02627
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- Ministry of Science and Technology (MOST) of the Republic of China [MOST 109-2113-M-194-008-MY2]
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The asymmetric total syntheses of (+)-5-epi-schisansphenin B and the proposed structure of (+)-15-hydroxyacora4(14),8-diene have been successfully accomplished in eight synthetic steps from 1,3-cyclopentadione. The enantioselective palladium-catalyzed redox-relay Heck alkenylation, the intramolecular Stetter reaction, and the regioselective Tiffeneau-Demjanov-type ring expansion played crucial roles in these syntheses.
The asymmetric total syntheses of (+)-5-epi-schisansphenin B and the proposed structure of (+)-15-hydroxyacora4(14),8-diene have been accomplished from 1,3-cyclopentadione (10) in eight synthetic steps. The enantioselective palladium-catalyzed redox-relay Heck alkenylation, the intramolecular Stetter reaction, and the regioselective Tiffeneau-Demjanov-type ring expansion were the pivotal steps in these syntheses.
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