10091-92-6

Usage

InChI:InChI=1/C18H10O5/c19-15-13(10-6-2-1-3-7-10)17(20)23-16(15)14-11-8-4-5-9-12(11)22-18(14)21/h1-9,20H/b16-14+

Upstream product

• 67-56-1 methanol 
• 6273-79-6 Pulvinic acid lacton 
• 27798-60-3 methyl 2-(2-methoxyphenyl)acetate 
• 866556-34-5 1-Methoxy-2-{(Z)-3-methoxy-1-[1-methoxy-1-trimethylsilanyloxy-meth-(Z)-ylidene]-2-trimethylsilanyloxy-allyl}-benzene 
• 866556-33-4 (Z)-4-Methoxy-2-(2-methoxy-phenyl)-3-trimethylsilanyloxy-but-2-enoic acid methyl ester 
• 866556-32-3 4-methoxy-2-(2-methoxy-phenyl)-3-oxo-butyric acid methyl ester 
• 6200-02-8 (3-methoxy-5-oxo-4-phenyl-5H-furan-2-ylidene)-(2-methoxy-phenyl)-acetic acid methyl ester 

Relevant academic research and scientific papers

Chemical constituents of the lichen, Candelaria concolor: A complete NMR and chemical degradative investigation

A detailed chemical and spectroscopic investigation of the terrestrial lichen Candelaria concolor has yielded several lichenic metabolites belonging to the pulvinic acid series, as well as several depside derivatives including pulvinic dilactone (1), vulpinic acid (4) and calycin (5). The chemical transformation of 1 to pulvinic acid (3) is reported for the first time, as is the conversion of atranorin (6) to 5-chloroatranorin (7) and then finally to 5,5'-dichloroatranorin (8) under very mild conditions. Also presented is the complete 1D and 2D NMR assignment for compounds 1, 3, 4, 5 and 8, including partial NMR chemical shift assignments for the unstable depside (7). Previously, these metabolites had only been partially assigned by NMR spectroscopy.

Synthesis of leprapinic acid, calycine and analogues by sequential "[3+2] cyclization/suzuki/lactonization" reactions

Calycine and analogues were prepared on the basis of Suzuki cross-coupling reactions of γ-alkylidene-α-hydroxybutenolides - readily available by cyclization of 1,3-dicarbonyl dianions or 1,3-bis(silyl enol ether)s with oxalyl derivatives - and subsequent boron tribromide-mediated lactonization. Leprapinic acid was prepared by chemoselective boron tribromide-mediated deprotection of permethylated leprapinic acid. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.