A stereoconvergent synthesis of (+)-4-demethoxydaunomycin |
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Authors: | A.V. Rama Rao J.S. Yadav K. Bal Reddy A.R. Mehendale |
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Affiliation: | National Chemical Laboratory, Poona 411008, India |
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Abstract: | Sharpless kinetic asymmetric epoxidation on (±)-2-(l-hydroxyethyl)-5,8-dimethoxy-3,4-dihydronaphthalene (8) followed by LAH reduction gave R-2-(S-l-hydroxyethyl)-2hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene and the undesired antipode. The former was converted to R-(-)-2-acetyl-2 hydroxy-5,8-dimethoxy-l,2,3,4-tetrahydronapthalen[R-(-)-5],while the latter was epimerized and recycled. R-(-)-5 has been exploited for the synthesis of(+)-4-demethoxydaunomycin |
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