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A convergent and enantioselective total synthesis of the most active isomer of beraprost was achieved in 17 pots. A unique tricyclic core in beraprost was synthesized efficiently by utilizing the… Click to show full abstract
A convergent and enantioselective total synthesis of the most active isomer of beraprost was achieved in 17 pots. A unique tricyclic core in beraprost was synthesized efficiently by utilizing the asymmetric organocatalyst-mediated formal [3 + 2] cycloaddition reaction of succinaldehyde with nitroalkene as a key step. The synthesis of the optically active Horner-Wadsworth-Emmons reagent for the construction of the ω-side chain was also established by means of the enantioselective Michael reaction of crotonaldehyde with nitromethane catalyzed by the organocatalyst developed by our group.
Journal Title: Organic letters
Year Published: 2017
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