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1 article(s) from Van Calenbergh, Serge

Synthesis of pyrrolidine-based hamamelitannin analogues as quorum sensing inhibitors in Staphylococcus aureus

Jakob Bouton,
Kristof Van Hecke,
Reuven Rasooly and
Serge Van Calenbergh

Beilstein J. Org. Chem. 2018, 14, 2822–2828, doi:10.3762/bjoc.14.260

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Figure 1: Structures of hamamelitannin (1), lead compound 2 and target compounds 3.

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Scheme 1: Proposed strategy for the synthesis of the target analogues.

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Scheme 2: Synthesis of fragment 9. Reagents and conditions: a) phthalimide, Pd₂(allyl)₂Cl₂, ligand 15, Na₂CO₃...

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Scheme 3: Synthesis of fragment 10. Reagents and conditions: a) TBSCl, NaH, THF, rt; b) phthalimide, PPh₃, DE...

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Scheme 4: Coupling of 9 and 10 and attempted ring-closing metathesis. Reagents and conditions: a) PPh₃, DEAD,...

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Scheme 5: Synthesis of alternative eastern fragment 23. Reagents and conditions: a) TBSCl, imidazole, CH₂Cl₂,...

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Scheme 6: Synthesis of 4. Reagents and conditions: a) PPh₃, DEAD, THF, 0 °C to rt; b) Grubbs–Hoveyda II (5 mo...

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Scheme 7: Late stage functionalization of the pyrrolidine nitrogen. Reagents and conditions: A) (masked) alde...

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Figure 2: Molecular X-ray structure of 3a, showing thermal displacement ellipsoids at the 50% probability lev...

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Published 12 Nov 2018

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