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[摘要]：The enantiodivergent synthesis of the Streptomyces alkaloid 4-epi-SS20846A was based on a Takai lefination/Suzuki-Miyaura coupling sequence for the highly stereoselective introduction of the E, E-pentadienyl side chain on the piperidine skeleton. Optical separation of a key hydroxylated enamide ester, prepared by palladium-catalyzed methoxycarbonylation of a lactam-derived enol phosphate, was successfully achieved by both lipase-catalyzed kinetic resolution and semipreparative HPLC. This approach allowed us to obtain the enantiopure target alkaloid in 35-38% yield over six steps. |
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