Synergistic Contribution of Tiglate and Cinnamate to Cytotoxicity of Ipomoeassin F
by Zong, G. H.; Whisenhunt, L.; Hu, Z. J.; Shi, W. Q.
An efficient synthetic route for ipomoeassin F and its tiglate-modified analogues was developed. The route features late-stage conformation-controlled highly regioselective esterification of the glucose diol in the disaccharide core. The results from the NCI-60 cell line screens of ipomoeassin F were reported for the first time. Moreover, two new C-3-cinnamoyl-Glcp analogues (2 and 3) were prepared. Their in-house cytotoxicity data convey an important message that both identity and positioning of the two alpha,beta-unsaturated esters are crucial. They are not interchangeable.
- Journal
- Journal of Organic Chemistry
- Volume
- 82
- Issue
- 9
- Year
- 2017
- Start Page
- 4977-4985
- URL
- https://dx.doi.org/10.1021/acs.joc.7b00409
- ISBN/ISSN
- 1520-6904; 0022-3263
- DOI
- 10.1021/acs.joc.7b00409