Infoscience

Journal article

Enantioselective Synthesis of (R)-(-)-2-Acetyl-2,5,12-Trihydro-1,2,3,4-Tetrahydro-6,11-Naphthacenequin One Via Diastereoselective Diels-Alder Cycloaddition

The BF3.Et2O-promoted Diels-Alder addition of 1-acetylvinyl (1'R,5'S,7'R)-3'-ethyl-2'-oxo-3'-aza-6',8'-dioxabicyclo[3.2.1]octane-7'- carboxylate (1-acetylvinylRADO(Et)) to 1-(dimethocymethyl)-2,3,5,6-tetramethylidene-7-oxabicyclo[2.2.1]heptane was highly regio-, stereo and diastereoselective giving a monoadduct that was converted into (R)-(-)4-demethoxy-7-deoxydaunomycinone.

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