15853-98-2

Upstream product

• 15853-98-2 usnic acid 
• 72056-29-2 (-)-pseudoplacodiolic acid 
• 21402-58-4 7,9-O,O-diacetylusnic acid 
• 64-19-7 acetic acid 
• 911794-63-3 7,9-diacetoxy-2,6-diacetyl-3-hydroxy-9,9b-dimethyl-9bH-dibenzofuran-1-one 
• 7664-93-9 sulfuric acid 
• 2657-28-5 2,4,6-trihydroxy-3-methyl-acetophenon 
• 1005771-13-0 usimine A 
• 95713-52-3 N-(2,4-dinitro-5-fluorophenyl)-L-alaninamide 
• 1005771-14-1 usimine B 
• 1005771-15-2 usimine C 

Downstream Products

• 62495-85-6 8-acetyl-5,7-dihydroxy-3,4a,6-trimethyl-1-phenyl-1,4a-dihydro-4H-benzofuro[3,2-f]indazol-4-one 
• 18058-88-3 2,6-diacetyl-3,7,9-trihydroxy-8,9b-dimethyl-4a,9b-dihydro-4H-dibenzofuran-1-one 
• 89352-63-6 usnic acid ethoxide 
• 21402-79-9 Decarbousnetic acid 
• 1064690-23-8 6-acetyl-2-[1-(1-carboxy-2-phenylethylamino)ethylidene]-7,9-dihydroxy-8,9b-dimethyl-1,2,3,9b-tetrahydrodibenzo[b,d]furan-1,3-dione 
• 1217276-06-6 (E)-6-acetyl-2-(1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylamino)ethylidene)-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bH)-dione 
• 1217276-10-2 (E)-2-(1-(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propylamino)ethylidene)-6-((E)-1-(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propylimino)ethyl)-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bH)-dione 
• 1217276-04-4 (E)-6-acetyl-2-(1-(3-(3,5-di-t-butyl-4-hydroxyphenyl)propylamino)ethylidene)-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bH)-dione 
• 1217276-11-3 (2E)-2-(1-(3,5-di-tert-butyl-4-hydroxyphenethylamino)ethylidene)-6-(1-(3,5-di-tert-butyl-4-hydroxyphenethylimino)ethyl)-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bH)-dione 
• 1217276-05-5 (E)-6-acetyl-2-(1-(3,5-di-t-butyl-4-hydroxyphenethylamino)ethylidene)-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bH)-dione 
• 1217276-08-8 (E)-6-acetyl-2-(1-(4-chlorophenylamino)ethylidene)-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bh)-dione 
• 1217276-09-9 (E)-6-acetyl-2-(1-(4-bromophenylamino)ethylidene)-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bh)-dione 
• 1316854-82-6 (-)-1-((4R,4aS)-4,5,7-trihydroxy-3,4a,6-trimethyl-1-phenyl-4,4a-dihydro-1H-benzofuro[3,2-f]indazol-8-yl)ethanone 

Relevant academic research and scientific papers

Usimines A-C, bioactive usnic acid derivatives from the antarctic lichen Stereocaulon alpinum

Usimines A-C (1-3), three new usnic acid derivatives, have been isolated from a MeOH extract of the Antarctic lichen Stereocaulon alpinum by various chromatographic methods. The structures of 1-3 were determined by analysis of their spectroscopic data (NMR, UV, MS) and by chemical methods. The known compound usnic acid (4) was also obtained. Compounds 1-4 showed moderate inhibitory activity against therapeutically targeted protein tyrosine phosphatase 1B (PTP1B).

The chemoenzymatic synthesis of usnic acid

Usnic acid, a highly functionalized dibenzofuran, is a polyketide secondary metabolite produced by several species of lichens. Synthesis of usnic acid from commercially available starting material was accomplished in two steps. The synthesis involves the methylation of phloracetophenone followed by oxidation with horseradish peroxidase. This work will lay the foundation for further biosynthetic studies on usnic acid.