740813-36-9Relevant academic research and scientific papers
Total Synthesis of Lamellarins U and A3 by Interrupting Halogen Dance
Mori, Atsunori,Okano, Kentaro,Okui, Yuya,Yasuda, Yuto
, (2022/03/09)
A total synthesis of lamellarins U and A3 is described. The synthesis features the interruption of a halogen dance reaction of a metalated β-dibromopyrrole. The pyrrolylmagnesium reagent, generated by deprotonative metalation by using (TMP)MgCl LiCl (TMP = 2,2,6,6-tetramethylpiperidide) as the base, was transmetalated to the corresponding organozinc species without causing the halogen dance reaction, which underwent a Negishi coupling to incorporate an aryl group onto the pyrrole ring. The arylated β-dibromopyrrole was then converted into lamellarins U and A3 through an -selective halogen magnesium exchange followed by carboxylation and subsequent palladium- mediated cyclization. The late-stage introduction of another aryl group was performed using a Kosugi Migita Stille coupling to provide lamellarins U and A3.
