187458-50-0

Upstream product

• 1005-56-7 phenylcarbonochloridothioate 
• 187458-49-7 C₂₆H₃₄O₅ 
• 187458-30-6 5-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-but-(Z)-ylidene]-4-methoxy-3-methyl-5H-furan-2-one 
• 187458-31-7 5-[(S)-4-Hydroxy-2-methyl-but-(Z)-ylidene]-4-methoxy-3-methyl-5H-furan-2-one 
• 1027414-45-4 Methanesulfonic acid (S)-4-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxy-4-methyl-5-oxo-2,5-dihydro-furan-2-yl)-2-methyl-butyl ester 
• 1026583-53-8 5-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-methyl-butyl]-4-methoxy-3-methyl-5H-furan-2-one 
• 187458-29-3 (2S, 3S)-5-(tert-butyldiphenylsilyloxy)-3-methylpentane-1,2-diol 
• 169387-99-9 (S)-2-methyl-4-(tert-butyldiphenylsilyloxy)butanol 
• 187458-37-3 methyl (2E,4E)-8-(3-furyl)-5-methyl-2,4-octadienate 
• 187458-45-3 3-((4E,6E)-9,9-Dibromo-4-methyl-nona-4,6,8-trienyl)-furan 
• 187458-25-9 (1E,3E,5E)-9-(3-furyl)-1-iodo-2,6-dimethyl-1,3,5-nonatriene 
• 187458-24-8 (S)-4-[3-Methoxy-4-methyl-5-oxo-5H-furan-(2Z)-ylidene]-3-methyl-butyraldehyde 
• 187458-40-8 (2E,4E)-8-(3-furyl)-5-methyl-2,4-octadien-1-ol 
• 187458-42-0 (2E,4E)-8-(3-furyl)-5-methyl-2,4-octadienal 

Downstream Products

• 63555-48-6 (-)-ircinianin 

Relevant academic research and scientific papers

Total synthesis of (-)-ircinianin and (+)-wistarin

(-)-Ircinianin (1), a cyclic furanosesterterpenetetronic acid isolated from a marine sponge (genus Ircinia), is synthesized in 17 steps from (S)-2-methylpropane-1,3-diol mono THP ether 10 and 3-furfural. The key step involves a NiCl2-CrCl2-mediated coupling reaction of iodotriene 9 with chiral aldehyde 8 in DMSO and subsequent intramolecular Diels-Alder reaction in one pot. Both reactions proceed very smoothly at room temperature and eventually give the cyclic product 30A possessing the desired cyclic skeleton of 1 in 60% yield. The structure of 30A is determined by X-ray crystallographic analysis. The stereochemistry of Diels-Alder reactions of 7A and another acyclic precursor 7B are discussed. The first total synthesis of (+)-wistarin (2) is accomplished in 55% yield by iodoether ring formation of 1 and hydrogenolysis of the iodide 33A. Based on the coupling constant in the proton NMR spectrum of 33A, the reported structure 2A is revised to 2B.