Synergistic Contribution of Tiglate and Cinnamate to Cytotoxicity of Ipomoeassin F.

Guanghui Zong, Lucas Whisenhunt, Zhijian Hu, Wei Q Shi

The Journal of organic chemistry 2017 May 05

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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 α,β-unsaturated esters are crucial. They are not interchangeable.

Citation

Guanghui Zong, Lucas Whisenhunt, Zhijian Hu, Wei Q Shi. Synergistic Contribution of Tiglate and Cinnamate to Cytotoxicity of Ipomoeassin F. The Journal of organic chemistry. 2017 May 05;82(9):4977-4985