Tetrahedron

Approaches to the regiospecific synthesis of anthracycline antibiotics

JE Baldwin, AJ Rajeckas

Index: Baldwin, Jack E.; Rajeckas, Algis J. Tetrahedron, 1982 , vol. 38, # 20 p. 3079 - 3084

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Citation Number: 7

Abstract

Synthetic approaches to anthracycline antibiotics were studied through the use of Claisen rearrangements on 1-methallyloxy-5-methoxyantraquinone (9) which required reducing conditions to proceed through a hydroquinone intermediate in situ. 1-(2′-Methylene-4′- pentenoxy)-5-methoxyanthraquinone (13) underwent a similar reductive rearrangement but also produced a spiro compound 16 as a result of an ene reaction between the phenol ...

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