549-23-5

Usage

Uses

Sclerotiorin is a natural product isolated primarily from?Penicilliumspecies.

InChI:InChI=1/C21H23ClO5/c1-6-12(2)9-13(3)7-8-15-10-16-17(11-26-15)19(24)21(5,27-14(4)23)20(25)18(16)22/h7-12H,6H2,1-5H3/b8-7+,13-9+/t12-,21+/m0/s1

Upstream product

• 1358912-14-7 C₂₁H₂₄O₅ 
• 7149-92-0 2,4-dimethoxy-3-methylbenzaldehyde 
• 1277176-10-9 C₁₉H₂₂O₃ 
• 1277176-12-1 2-iodo-4,6-dihydroxy-5-methylbenzaldehyde 
• 915789-22-9 6-ethynyl-2,4-dihydroxy-3-methylbenzaldehyde 
• 1448460-82-9 C₁₉H₂₃O₃⁽¹⁺⁾*C₇H₇O₃S^(1-) 

Downstream Products

• 64-18-6 formic acid 
• 127353-38-2 (+)-(2E,4E,6S)-4,6-dimethylocta-2,4-dienoic acid 

Relevant academic research and scientific papers

PRODUCTION OF LIPOXYGENASE INHIBITORS VIA FUNGAL BIOSYNTHETIC PATHWAY

The invention provides methods for producing lipoxygenase inhibitors including the steps set forth in Schemes 2 and 3, and uses of the inhibitors produced by the methods set forth herein in to treat various disease states.

Reengineering an azaphilone biosynthesis pathway in Aspergillus nidulans to create lipoxygenase inhibitors

Sclerotiorin, an azaphilone polyketide, is a bioactive natural product known to inhibit 15-lipoxygenase and many other biological targets. To readily access sclerotiorin and analogs, we developed a 2-3 step semisynthetic route to produce a variety of azaphilones starting from an advanced, putative azaphilone intermediate (5) overproduced by an engineered strain of Aspergillus nidulans. The inhibitory activities of the semisynthetic azaphilones against 15-lipoxygenase were evaluated with several compounds displaying low micromolar potency.

Synthesis of the azaphilones (+)-sclerotiorin and (+)-8- O -methylsclerotiorinamine utilizing (+)-sparteine surrogates in copper-mediated oxidative dearomatization

Enantioselective syntheses of the azaphilone natural products (+)-sclerotiorin and (+)-8-O-methylsclerotiorinamine that possess the natural R-configuration at the quaternary center are reported. The syntheses were accomplished using copper-mediated asymmetric dearomatization employing bis-i-oxo copper complexes prepared from readily available (+)-sparteine surrogates. Of note, site-selective O-methylation of a vinylogous pyridone was used to access the isoquinolin-6(7H)-one core of (+)-8-O- methylsclerotiorinamine.