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A highly enantioselective synthesis of (R)-(-)-2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthol. A key intermediate in the synthesis of anthracyclinones
Journal article   Peer reviewed

A highly enantioselective synthesis of (R)-(-)-2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthol. A key intermediate in the synthesis of anthracyclinones

Franklin A. Davis, Anil Kumar and Bang-Chi Chen
Tetrahedron letters, v 32(7), pp 867-870
1991

Abstract

AB-Synthon (R)-(−)- 5, a key intermediate in the asymmetric synthesis of anthracyclinones 3 and 4 is prepared in 35% overall yield and > 95% ee. The key step involves hydroxylation of the potassium enolate of 7 using N-sulfonyloxaziridine (−)- 6c. AB-Synthon (R)- 5, a key intermediate in the synthesis of the antitumor anthracyclinones, was prepared in 35% overall yield in > 95% ee via the enantioselective hydroxylation of the β-ketoester potassium enolate using N-sulfonyloxazridine (-)- 6

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Web of Science research areas
Chemistry, Organic
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