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The Enantioselective Total Synthesis of (+)-3-Ketobrassicicene W and (-)-Alterbrassicicene B
Weston C Bonnet1, Noah J Sims1, Joseph P Tuccinardi1
1Department of Chemistry and Biochemistry, Baylor University, One Bear Place 97348, Waco, Texas 76798, United States.
Abstract:
Herein the first enantioselective total synthesis of the C16-nor-fusicoccane diterpenoids (+)-3-ketobrassicicene W and (-)-alterbrassicicene B is described. The strategy evolved from our recent synthesis of (+)-alterbrassicicene C and leveraged the convergent union of two enantioenriched cyclopentene fragments. Substrate controlled stereoselectivity guided the route through hydration, oxidation and reduction steps to deliver (+)-3-ketobrassicicene W which was converted to (-)-alterbrassicicene B upon Lewis acid induced transannular oxa-Michael addition.
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