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DOI: 10.1055/s-0037-1610287
A Synthetic Route to the MT1-MMP Inhibitor Ancorinoside D
Publikationsverlauf
Received: 04. Juli 2018
Accepted after revision: 29. August 2018
Publikationsdatum:
26. September 2018 (online)
Abstract
A methyl ester of ancorinoside D, a 3-acyltetramic acid metabolite of a sponge Penares sollasi, was synthesised in ten steps starting from a protected β-d-glucopyranosyl-(1→4)-d-galactopyranosyltrichloroacetimidate donor. Its attachment to the left half of the 3-acyl spacer by a Schmidt glycosylation, 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)-mediated oxidation to the uronic acid, introduction of the Z-alkene via Wittig reaction, and functionalisation of the spacer terminus with Meldrum’s acid gave a β-keto ester that reacted with dimethyl N-methyl-d-aspartate under neutral conditions to afford a fully protected ancorinoside D as the product of an unusual domino N-acylation–Dieckmann condensation. Global deprotection left a methyl ester of ancorinoside D, which resisted all saponification attempts.
Key words
tetramic acid - Wittig reaction - Dieckmann cyclisation - natural products - glycosylation - ancorinoside - MMP inhibitor - domino reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610287.
- Supporting Information
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