Abstract
Cross coupling reactions of lithiated 2,5-piperazinedione anions with gramine methosulfate and alkylhalides were shown to be catalyzed by copper reagents, e.g. dilithium tetrachlorocuprate and copper (I) iodide. Based on this findings, the results of the first method for preparation of racemic thaxtomins are reported. Compound 1c, chosen as a synthetic model, was prepared in five steps in 19% overall yield. The key step was reaction of the lithiated anion of sarcosine anhydride with gramine methosulfate in the presence of a catalytic amount of dilithium tetrachlorocuprate in THF. The remainder of the sequence involved protection of the indole NH, aldol condensation with 3-benzyloxybenzaldehyde, bromohydrin formation and catalytic hydrogenation.
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.
