Synergistic Contribution of Tiglate and Cinnamate to Cytotoxicity of Ipomoeassin F

摘要

src="http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/joceah/2017/joceah.2017.82.issue-9/acs.joc.7b00409/20170501/images/medium/jo-2017-004097_0009.gif">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.