Synthesis of pluraflavin A "aglycone" Journal Article
| Authors: | Wright, B. J. D.; Hartung, J.; Peng, F.; Van De Water, R.; Liu, H.; Tan, Q. H.; Chou, T. C.; Danishefsky, S. J. |
| Article Title: | 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 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. © 2008 American Chemical Society. |
| Keywords: | unclassified drug; doxorubicin; cell proliferation; drug structure; cell line, tumor; drug synthesis; cytotoxic; drug cytotoxicity; olefins; diels alder reaction; in vitro; complexation; cycloaddition; synthesis of; cyanides; aglycone; d rings; dipolar cycloaddition; en routes; isoxazoline; key features; nanomolar ranges; nitrile oxides; title compounds; nitrogen oxides; pluraflavin a; anthraquinones |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 130 |
| Issue: | 49 |
| ISSN: | 0002-7863 |
| Publisher: | American Chemical Society |
| Date Published: | 2008-12-10 |
| Start Page: | 16786 |
| End Page: | 16790 |
| Language: | English |
| DOI: | 10.1021/ja805936v |
| PUBMED: | 19049469 |
| PROVIDER: | scopus |
| PMCID: | PMC2638005 |
| DOI/URL: | |
| Notes: | --- - "Cited By (since 1996): 8" - "Export Date: 17 November 2011" - "CODEN: JACSA" - "Source: Scopus" |
Altmetric
Citation Impact
BMJ Impact Analytics
MSK Authors
-
3Liu -
539Danishefsky -
319Chou -
4
Tan
Related MSK Work