124010-10-2Relevant articles and documents
Preparation of Functionalized Juglone Acetates and Juglones via 1,4-Dimethoxynaphthalene Derivatives: Synthesis of Anthraquinones Related to Rhein and Aloe Emodin
Bloomer, James L.,Stagliano, Kenneth W.,Gazzillo, Joseph A.
, p. 7906 - 7912 (1993)
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Synthesis of pluraflavin A "aglycone"
Wright, Benjamin J. D.,Hartung, John,Peng, Feng,Van De Water, Ryan,Liu, Haibo,Tan, Quen-Hui,Chou, Ting-Chao,Danishefsky, Samuel J.
supporting information; experimental part, p. 16786 - 16790 (2009/04/14)
The "aglycone" of pluraflavin A (2) has been synthesized. The key features of this synthesis include a 1,3-dipolar cycloaddition between a nitrile oxide (cf. 14) and an olefin (22) to yield an isoxazoline followed by subsequent conversion into the γ-pyrone of pluraflavin A. The epoxide moiety linked to the pyrone is installed prior to Diels-Alder installation of the D ring, which allows access to a number of potentially active cytotoxic intermediates en route to the final compound. The preliminary in vitro results of two such compounds are also included with the racemic title compound exhibiting cytotoxicity in the nanomolar range.