title: Modular enantioselective synthesis of 8-aza-prostaglandin E1.
abstract: We report herein for the first time the enantioselective synthesis of 8-aza-PGE1. The synthesis used the cross olefin metathesis reaction to connect the 5-vinyl-γ-lactam subunit, prepared from (R)-malic acid via the Ley's sulfone-based α-amidalkylation protocol (dr = 6.8:1), with the chiral pre-ω-chain. The latter was synthesized in high enantioselectivity from (E)-2-octenol by the Sharpless asymmetric epoxidation and the titanocene-mediated epoxide opening. This modular approach is quite concise and flexible, and requires only eight steps from commercially available reagents.
authors: Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University , Xiamen, Fujian 361005, P. R. China.
authors: Xiao-Gang
authors: XG
authors: Wang
authors: Ai-E
authors: AE
authors: Wang
authors: Yi
authors: Y
authors: Hao
authors: Yuan-Ping
authors: YP
authors: Ruan
authors: Pei-Qiang
authors: PQ
authors: Huang
mesh_terms: D000527:Alprostadil / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C028327:8-azaprostaglandin E1; D000527:Alprostadil