Synergistic Contribution of Tiglate and Cinnamate to Cytotoxicity of Ipomoeassin F
by Zong, Guanghui; Whisenhunt, Lucas; Hu, Zhijian; Shi, Wei
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 of Organic Chemistry
- Start Page
- 0022-3263; 1520-6904