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

Comprehensive Summary Herein, a highly enantioselective formal synthesis of (+)‐Treprostinil via the interphenylene prostaglandin E 1 scaffold was described. The chiral multi‐substituted cyclopentanone was constructed via a [Rh(Duanphos)SbF 6 ‐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.

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Publication Details

Journal
Chinese Journal of Chemistry
Published
2025-04-30
DOI
https://doi.org/10.1002/cjoc.70043
Citations
3
Primary Topic
Catalytic Alkyne Reactions
Type
article
Field-Weighted Citation Impact
2.81

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article

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

Gen‐Qiang Chen, Xiaomei Zou, Xumu Zhang, Yan Zong et al.
3 citations
Chinese Journal of Chemistry
Catalytic Alkyne Reactions
2.81
article

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

Gen‐Qiang Chen, Xiaomei Zou, Xumu Zhang, Yan Zong, Shuang Gao, Qiuchen Huang
article en
3 citations

Abstract

Comprehensive Summary Herein, a highly enantioselective formal synthesis of (+)‐Treprostinil via the interphenylene prostaglandin E 1 scaffold was described. The chiral multi‐substituted cyclopentanone was constructed via a [Rh(Duanphos)SbF 6 ‐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.

Chinese Journal of ChemistryVol. 43(15)
Southern University of Science and Technology (CN), Ji Hua Laboratory (CN), University of Hong Kong (HK)
National Natural Science Foundation of China, National Key Research and Development Program of China
Clean water and sanitation
Openalex Percentile: Top 11%
Catalytic Alkyne Reactions
2.81
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