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1 article(s) from Mikula, Hannes

Synthesis of zearalenone-16-β,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugation

Hannes Mikula,
Julia Weber,
Dennis Svatunek,
Philipp Skrinjar,
Gerhard Adam,
Rudolf Krska,
Christian Hametner and
Johannes Fröhlich

Beilstein J. Org. Chem. 2014, 10, 1129–1134, doi:10.3762/bjoc.10.112

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Graphical Abstract

Figure 1: Structure of selected RAL type fungal secondary metabolites.

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Figure 2: Structures of zearalenone conjugates: (A) ZEN-14-β,D-glucoside (5) and ZEN-14-sulfate (6), (B) ZEN-...

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Scheme 1: General strategy for the synthesis of RAL-2’-conjugation (Pg: protective group, pGlc: protected glu...

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Scheme 2: (A) Regioselective acetylation of resorcylic acid ester 9. (B) Lewis acid mediated glucosylation; n...

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Scheme 3: Regioselective acetylation of ZEN (1) affording 14-O-acetylzearalenone (14).

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Scheme 4: (A) Regioselective p-methoxybenzylation of 9. (B) Synthesis of the ZEN-16-Glc mimic 17.

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Scheme 5: Regioselective protection of ZEN (1) and failed PMB cleavage of the glucosylated intermediate 19.

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Scheme 6: Synthesis of (A) ZEN mimic glucoside 17 and (B) ZEN-16-β,D-glucoside (7); a: TIPS-Cl, imidazole, 16...

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Scheme 7: Chemical sulfation using the 2,2,2-trichloroethyl (TCE)-protected sulfuryl imidazolium salt 23 yiel...

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Published 15 May 2014

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