Journal
SYNTHESIS-STUTTGART
Volume 54, Issue 11, Pages 2647-2660Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/a-1736-7337
Keywords
lamellarins; halogen dance; pyrroles; alkaloids; total synthesis; lithiation; metalation; deprotonation
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Funding
- Japan Society for the Promotion of Science [JSPS, KAKENHI] [JP19H02717]
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A total synthesis of lamellarins U and A3 is described. The synthesis involves the interruption of a halogen dance reaction and the incorporation of an aryl group onto the pyrrole ring. The final products are obtained through a series of reactions.
A total synthesis of lamellarins U and A3 is described. The synthesis features the interruption of a halogen dance reaction of a metalated alpha,beta-dibromopyrrole. The pyrrolylmagnesium reagent, generated by deprotonative metalation by using (TMP)MgCl center dot 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 alpha,beta-dibromopyrrole was then converted into lamellarins U and A3 through an alpha-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.
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