Synthesis of an Advanced Intermediate for Leustroducsins and Phoslactomycins Synthesis by Heterocycloaddition

Submitting author affiliation:
Université Paris-Saclay, Orsay, France

Beilstein Arch. 2022, 202269.

Published 23 Aug 2022

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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 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 vinyl lithium intermediate.  An advanced synthetic intermediate was then obtained after functional group transformation.

Keywords: Total synthesis; stereoselective; cycloaddition; organolithium

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Rousseau, A.; Vincent, G.; Kouklovsky, C. Beilstein Arch. 2022, 202269. doi:10.3762/bxiv.2022.69.v1

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