147589-46-6Relevant articles and documents
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.
Directable regiochemistry in naphthazarins via the use of masked derivatives
Bloomer,Stagliano
, p. 757 - 760 (2007/10/02)
The carboethoxynaphthol 3d was converted via salcomine oxidation to the masked carboethoxynaphthazarin 4b which could undergo nucleophilic addition or, if unmasked, transfer quinone reactivity to the alternative ring in form 5. The latter should undergo regiospecific Diels-Alder reactions.
