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Enantioselective Total Synthesis of Beraprost Using Organocatalyst
Shigenobu Umemiya1, Daisuke Sakamoto1, Genki Kawauchi1
1Department of Chemistry, Graduate School of Science, Tohoku University , 6-3 Aramaki-Aza, Aoba, Aoba-ku, Sendai, Miyagi 980-8578, Japan.
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.
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