121637-75-0

Upstream product

• 121637-74-9 2-benzyloxy-5,8-dimethoxy-2-(1-hydroxyethyl)-1,2,3,4-tetrahydronaphthalene 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 112997-44-1 2-hydroxymethyl-5,8-dimethoxy-3,4-dihydronaphthalene 
• 121637-70-5 2-hydroxy-2-hydroxymethyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene 
• 121702-30-5 (4,7-Dimethoxy-3,7b-dihydro-2H-1-oxa-cyclopropa[a]naphthalen-1a-yl)-methanol 
• 121637-72-7 2-benzyloxy-2-hydroxymethyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene 
• 121637-73-8 2-benzyloxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-2-aldehyde 
• 121637-71-6 C₂₀H₂₂O₄ 

Downstream Products

• 65529-77-3 4-demethoxy-7-deoxydaunomycinone 

Relevant academic research and scientific papers

Model Studies for an Asymmetric Synthesis of (+)-4-Demethoxydaunomycinone

2-Hydroxymethyl-5,8-dimethoxy-3,4-dihydronaphthalene (II) on t-butyl hydroperoxide oxidation followed by LAH reduction gives 2-hydroxy-2-hydroxymethyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene (IVa) in 85percent yield.The corresponding O-benzyl derivate (VI) on PDC oxidation affords 2-benzyloxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthyl-2-aldehyde (VII), which on Grignard reaction with methylmagnesium iodide followed by PDC oxidation affords the desired (+/-)-2-acetyl-2-O-benzyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene (IXa) in 70percent yield.Friedel-Crafts condensation of IXa with phthalic anhydride in the presence of AlCl3-NaCl melt furnishes (+/-)-4-demethoxy-7-deoxydaunomycinone (Ia) in 74percent yield, which on 7-hydroxylation affords the desired (+/-)-4-demethoxydaunomycinone (Ib) in 40percent yield.