Highly Enantioselective Formal Synthesis of (+)-Treprostinil Enabled by Rhodium-Catalyzed Enyne Cycloisomerization

Yan Zong; Shuang Gao; Xiaomei Zou; Qiuchen Huang; Gen-Qiang Chen; Xumu Zhang

doi:10.1002/cjoc.70043

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (15) : 1783 -1788. DOI: 10.1002/cjoc.70043

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Highly Enantioselective Formal Synthesis of (+)-Treprostinil Enabled by Rhodium-Catalyzed Enyne Cycloisomerization

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Abstract

Herein, a highly enantioselective formal synthesis of (+)-Treprostinil via the interphenylene prostaglandin E₁ scaffold was described. The chiral multi-substituted cyclopentanone was constructed via a [Rh(Duanphos)SbF₆-catalyzed asymmetric enyne cycloisomerization and a copper hydride-mediated conjugate reduction. In addition, a new type of interphenylene prostaglandin scaffold was obtained via a formal Alder-ene reaction in high yield with excellent chemoselectivity.

Keywords

Enantioselective formal synthesis / Enyne cycloisomerization / Duanphos / (+)–Treprostinil / Cross metathesis

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Yan Zong, Shuang Gao, Xiaomei Zou, Qiuchen Huang, Gen-Qiang Chen, Xumu Zhang. Highly Enantioselective Formal Synthesis of (+)-Treprostinil Enabled by Rhodium-Catalyzed Enyne Cycloisomerization. Chinese Journal of Chemistry, 2025, 43(15): 1783-1788 DOI:10.1002/cjoc.70043