Preparation of functionalized juglone acetates and juglones via 1, 4-dimethoxynaphthalene derivatives: synthesis of anthraquinones related to rhein and aloe-emodin

JL Bloomer, KW Stagliano…

Index: Bloomer, James L.; Stagliano, Kenneth W.; Gazzillo, Joseph A. Journal of Organic Chemistry, 1993 , vol. 58, # 27 p. 7906 - 7912

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Citation Number: 37

Abstract

Since juglones have established themselves as important anthracycline and polyketide synthons, we became interested in efficient methods for their synthesis. In particular, we noted that the 3-halojuglones were of special importance since these had excellent regiochemistry in Diels-Alder reactions.'At the inception of our studies one of the most generally useful preparative procedures involved reaction of eilylated dienes2 with ...