Abstract
AbstractAttempts to induce the formation of the dibenzoxepine ring of cularine compounds by generating an electron‐deficient system in ring C of an 8‐hydroxybenzylisoquinoline met with failure. Attack by C‐8 phenol on a “p‐quinone methide” intermediate afforded benzofurans 16, which it has been suggested are intermediates in the biogenesis of quettamines. Among the nucleophilic substitution reactions tried, only that based on a phenoxide attack on a benzyne intermediate (generated by dimsyl sodium treatment of a 2′‐bromo‐8‐hydroxybenzylisoquinoline) afforded the dibenzoxepine nucleus of tetradehydrocularines 25 and 27. Competing N‐attack afforded the indolizine skeleton present in 24 and 26. From compounds 25 and 27, the corresponding cularines, cularimines and oxocularines were obtained.
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 callDisclaimer: 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.
