Asymmetric total synthesis of tricyclic prostaglandin D2 metabolite methyl ester via oxidative radical cyclization

• Miao Xiao,
• Liuyang Pu,
• Qiaoli Shang,
• Lei Zhu and
• Jun Huang

Beilstein J. Org. Chem. 2025, 21, 1964–1972, doi:10.3762/bjoc.21.152

• pathophysiological mediator in many human diseases and biological pathways. Tricyclic prostaglandin D2 metabolite methyl ester (tricyclic-PGDM methyl ester), the major urinary metabolite of PGD2, can be used as a clinical indicator for PGD2 overproduction. However, the limited amount of tricyclic-PGDM methyl ester

• synthesis of tricyclic-PGDM methyl ester in 9 steps and 8% overall yield. Keywords: asymmetric total synthesis; oxidative radical cyclization; tricyclic prostaglandin D2 metabolite methyl ester; Introduction Prostaglandins (PGs), a family of hormone-like lipid compounds, are ubiquitous natural products

• prostaglandin D2 metabolite methyl ester (tricyclic-PGDM methyl ester, 4), the major urinary metabolite of PGD2, has been used as an indicator for PGD2 overproduction. Roberts and associates established an assay for tricyclic-PGDM measurement using 18O-labelled tricyclic-PGDM methyl ester 8, which is an