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Synthesis of pluraflavin A "aglycone".

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.

SUBMITTER: Wright BJ

PROVIDER: S-EPMC2638005 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature

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Synthesis of pluraflavin A "aglycone".

Wright Benjamin J D BJ Hartung John J Peng Feng F Van de Water Ryan R Liu Haibo H Tan Quen-Hui QH Chou Ting-Chao TC Danishefsky Samuel J SJ

Journal of the American Chemical Society 20081201 49

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 preli ...[more]

PMID: 19049469

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