Literature DB >> 19049469

Synthesis of pluraflavin A "aglycone".

Benjamin J D Wright1, John Hartung, Feng Peng, Ryan Van de Water, Haibo Liu, Quen-Hui Tan, Ting-Chao Chou, Samuel J Danishefsky.   

Abstract

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 gamma-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.

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Year:  2008        PMID： 19049469      PMCID： PMC2638005          DOI： 10.1021/ja805936v

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


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