Synthetic Study of the Angular Tetracyclic Core Skeleton of Landmycine A via Masamune–Bergman Cyclization

Abstract

We describe the synthesis, via Masamune–Bergman cyclization, of an angucycline derivative involving a quinone in the B ring and a nonaromatic hydroxylated C ring. The naphthoquinone was synthesized via the copper-catalyzed Ullmann reaction of the dihalo aryl moiety, and the subsequent oxidation of a corresponding hydroquinone. The aryl dihalide was prepared by the dihalogenation of the 1,4-diradical generated during the Masamune–Bergman cyclization of the 1,2- dialkynylbenzene under neutral conditions. This methodology suggests a new route for the construction of natural products containing an anthraquinone skeleton.

Key words

aglycon - deoxyoligosaccharide - quinone - NHK coupling - Ullmann coupling

• References and Notes


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