Aureothin

• CAT Number: R003855
• CAS Number: 2825-00-5
• PubChem Substance ID: 6569946
• Molecular Formula: C22H23NO6
• Molecular Weight: 397.4
• Purity: 95%
• Synonyms: Antibiotic 74A;BRN 0058476;JA 2814K;Mycolutein;Strain 58 substance
• Target: HIV
• Appearance: Yellow solid
• Storage: -20°C
• Analysis method: HPLC
• IUPAC Name: 2-methoxy-3,5-dimethyl-6-[(2R,4Z)-4-[(E)-2-methyl-3-(4-nitrophenyl)prop-2-enylidene]oxolan-2-yl]pyran-4-one
• InChI: InChI=1S/C22H23NO6/c1-13(9-16-5-7-18(8-6-16)23(25)26)10-17-11-19(28-12-17)21-14(2)20(24)15(3)22(27-4)29-21/h5-10,19H,11-12H2,1-4H3/b13-9+,17-10-/t19-/m1/s1
• InChIKey: GQKXCBCSVYJUMI-WACKOAQBSA-N
• SMILES: CC1=C(OC(=C(C1=O)C)OC)C2CC(=CC(=CC3=CC=C(C=C3)[N+](=O)[O-])C)CO2

Aureothin, an unusual pyranone metabolite, has broad biological actions including antitumor, antimicrobial and insecticidal
activities. Aureothin acts by inhibiting oxidoreductase. More recently, aureothin has been shown to be a potent inhibitor of
Helicobacter pylori.

Reference

1. Chembiochem. 2012 Oct 15;13(15):2196-9. doi: 10.1002/cbic.201200406. Epub 2012
Sep 7.

Pyran formation by an atypical CYP-mediated four-electron oxygenation-cyclization
cascade in an engineered aureothin pathway.

Richter M(1), Busch B, Ishida K, Moore BS, Hertweck C.

Author information:
(1)Dept. Biomolecular Chemistry, Leibniz Institute for Natural Product Research
and Infection Biology, HKI, Beutenbergstrasse 11a, 07745 Jena, Germany.

Small changes, big effect: A new aureothin derivative, aureopyran, which features
an unusual pyran backbone, was generated by simply altering the enzymatic
methylation topology. The α-pyrone ring hampers the correct placement of the
polyketide backbone in the multifunctional cytochrome P450 monooxygenase AurH.
Instead of a tetrahydrofuran ring, an oxo intermediate is formed that readily
undergoes a rare electrocyclization reaction.

2. J Org Chem. 2016 Jun 17;81(12):5190-201. doi: 10.1021/acs.joc.6b00878. Epub 2016
May 27.

Flexible Total Synthesis of (±)-Aureothin, a Potent Antiproliferative Agent.

Henrot M(1), Jean A(1), Peixoto PA(1), Maddaluno J(1), De Paolis M(1).

Author information:
(1)COBRA-IRCOF, CNRS, Université & INSA de Rouen , Mont Saint Aignan, France.

Amenable to late-stage preparation of analogues, a flexible and convergent total
synthesis of (±)-aureothin is presented. The strategy was based on a
desymmetrization of α,α’-dimethoxy-γ-pyrone by a process combining 1,4-addition
and alkylation of vinylogous enolate to stereoselectively reach the backbone of
the target. Palladium-catalyzed cyanation of an elaborated and isomerizable E,Z
dienyl motif followed by Pinner cyclization enabled the construction of the
tetrahydrofuran motif while a first approach based on a late-stage oxidation was
unsuccessful.