1368604-15-2

Upstream product

• 24599-58-4 2,5-dimethoxy toluene 
• 814-68-6 acryloyl chloride 

Downstream Products

• 1350803-13-2 1-(2-hydroxy-5-methoxy-4-methylphenyl)prop-2-en-1-one 
• 1350803-25-6 C₂₂H₂₆O₅S 
• 1350803-16-5 tert-butyl (2-(1-hydroxy-3-(phenylthio)propyl)-4-methoxy-5-methylphenyl) carbonate 
• 1350803-17-6 (2R,2'S,4S,5'S)-6-methoxy-5',7-dimethyl-2'-phenethyl-4-(2-(phenylthio)ethyl)spiro[chroman-2,4'-[1,3]dioxolane] 
• 1350803-18-7 (S)-1-((2R,4S)-6-methoxy-7-methyl-4-(2-(phenylthio)ethyl)chroman-2-yl)ethanol 
• 1350803-21-2 (3R,5S,9aR)-2,2,8-trimethyl-5-vinyl-4,5-dihydro-2H-3,9a-epoxybenzo[b]oxepin-7(3H)-one 
• 1242430-87-0 2-((3S,5S)-5,6-dihydroxy-6-methylhept-1-en-3-yl)-5-methylcyclohexa-2,5-diene-1,4-dione 
• 1350803-23-4 2-((2S,4R)-4-hydroxy-5,5-dimethyl-2-vinyltetrahydrofuran-2-yl)-5-methylcyclohexa-2,5-diene-1,4-dione 
• 1350803-22-3 (2R,5S)-7-methoxy-3,3,8-trimethyl-5-vinyl-3,5-dihydro-2H-2,5-methanobenzo[e][1,4]dioxepine 
• 1350803-19-8 C₂₇H₂₉NO₇S₂ 

Relevant academic research and scientific papers

Total syntheses of ent-heliespirones A and C

Stereodivergent total syntheses of ent-heliespirone A and C were both completed in 11 vessels and ～24% combined overall yield (A + C). These syntheses employed an identical inverse demand Diels-Alder reaction between a surrogate for an extendedly conjugated γ-δ unsaturated ortho-quinone methide and l-lactic-acid-derived exocyclic enol ether. Novel reactions of special note include a diastereoselective reduction of a chroman spiroketal by combination of borontrifluoride etherate and triethyl silane, along with oxidative rupture of a chroman etherial ring into the corresponding p-quinone by argentic oxide (AgO). In addition, an unusual intramolecular etherification of a 3° alcohol caused by cerium ammonium nitrate was observed.