161141-55-5

Upstream product

• 116511-95-6 (benzenesulfonyl)methyllithium 
• 161141-53-3 4-(4,4-Dimethyl-5-oxopentyl)-6-methoxychroman-3-one 
• 43088-72-8 6-Methoxyisochroman-3-one 
• 128291-70-3 6-Iodo-3,3-dimethylhex-1-ene 
• 161141-47-5 6-Methoxy-4-(4,4-dimethylhex-5-enyl)isochroman-3-one 

Downstream Products

• 193215-67-7 (E)-8-Benzenesulfonyl-2-(2-formyl-5-methoxy-phenyl)-6,6-dimethyl-oct-7-enoic acid methyl ester 
• 193215-65-5 (E)-8-Benzenesulfonyl-2-(2-hydroxymethyl-5-methoxy-phenyl)-6,6-dimethyl-oct-7-enoic acid methyl ester 
• 161141-57-7 2-(2-Formyl-5-methoxyphenyl)-6,6-dimethyl-8-phenylsulfonyloct-7-enoic acid 

Relevant academic research and scientific papers

Intramolecular Diels-Alder additions to 2-benzopyran-3-ones; anti-selectivity induced by the phenylsulfonyl group

Intramolecular Diels-Alder additions of the 2-benzopyran-3-ones 2d, 2e and 2f with an E-SO2Ph substituent on the dienophile (X = SO2Ph in 2) show greatly enhanced exo-addition of the tether than is shown in the absence of the E-SO2Ph group (X = H in 2). For 2e and 2f, exo-chain addition becomes preferred, and for 2d, endo-chain addition much less preferred, than in related cases with X = H. An E-CO2Me group on the dienophile is also effective in enhancing exo-chain addition, but less effective than an E-SO2Ph group. The adducts 4e and 4f undergo reductive elimination (5% Na-Hg) to give the diterpene related products 32 and 33 respectively.

Intramolecular Diels-Alder additions to 2-benzopyran-3-ones; Anti-selectivity induced by the phenylsulfonyl group

The 2-benzopyran-3-ones 7a and 7c undergo intramolecular Diels-Alder addition via preferred endo-addition of the connecting chain, whereas for 7d and 7e (X = SO2Ph), exo-addition of the chain is preferred; the main adducts from the latter additions (9d and 9e), give the diterpene-related products 12 (R = H, Y = OMe) and 12 (R = Me, Y = OMe) upon treatment with sodium amalgam.