Abstract

AbstractThe reaction of protected 3‐bromo‐2‐(bromomethyl)‐4‐methoxypyrrolo[2,3‐b]pyridine and tosylmethyl isocyanide (TosMIC) afforded a pyrido[3′,2′:4,5]pyrrolo[1,2‐c]pyrimidine derivative in good yield. This compound was transformed through installation of the pyrimidine moiety in the C5 position, hydrolysis, and decarboxylation in an advanced intermediate for the total or formal synthesis of the naturalalkaloid variolin B. Reaction of 3‐bromo‐2‐(bromomethyl)‐4‐chloropyrrolo[2,3‐b]pyridine with N‐tosylmethyl dichloroformimide as a synthetic TosMIC equivalent afforded trihalo‐substituted pyrido[3′,2′:4,5]pyrrolo[1,2‐c]pyrimidine. This compound was used in a new total synthesis of the alkaloid variolin B by selective and sequential C–N, C–C, and C–O palladium‐mediated functionalization at the C9, C5, and C4 positions of the pyrido[3′,2′:4,5]pyrrolo[1,2‐c]pyrimidine system. A formal synthesis of deoxyvariolin B is also described by using the same synthetic strategy.

Talk to us

Join us for a 30 min session where you can share your feedback and ask us any queries you have

Schedule a call

Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.