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Preparation of an advanced intermediate for the synthesis of leustroducsins and phoslactomycins by heterocycloaddition

A convergent strategy for the synthesis of leustroducsins and phoslactomycins has been designed, relying on the synthesis and the coupling of three main fragments. The central fragment was synthesized via a regio-and stereoselective nitroso Diels–Alder reaction with an enol phosphate, followed by re...

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Detalles Bibliográficos
Autores principales: Rousseau, Anaïs, Vincent, Guillaume, Kouklovsky, Cyrille
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9551206/
https://www.ncbi.nlm.nih.gov/pubmed/36262671
http://dx.doi.org/10.3762/bjoc.18.143
Descripción
Sumario:A convergent strategy for the synthesis of leustroducsins and phoslactomycins has been designed, relying on the synthesis and the coupling of three main fragments. The central fragment was synthesized via a regio-and stereoselective nitroso Diels–Alder reaction with an enol phosphate, followed by reductive cleavage of the phosphate to the ketone 11b. Coupling studies of this fragment with the lactone fragment was accomplished in a stereoselective fashion through a vinyllithium intermediate. An advanced synthetic intermediate was then obtained after functional group transformation.