Buckler, JoshuaBanwell, MartinKordbacheh, FarzanehParish, ChristopherSantiago, FernandoKhachigian, Levon M2021-01-052021-01-052470-1343http://hdl.handle.net/1885/219095Stereoselective total syntheses of the four stereoisomeric forms of guaiacylglycerol 8-O-4′-coniferyl ether, viz., compounds 1, ent- 1, 2, and ent- 2, have been established. The key step involves an Evans/Seebach auxiliarycontrolled and syn-selective aldol process followed, in the reaction sequences leading to the anti-compounds, by a Mitsunobu reaction involving a benzylic alcohol residue. The proangiogenic properties of the synthetic materials were evaluated in a human microvascular endothelial cell tubule formation assay, thus revealing that they are all active, with the 8S-configured compounds 1 and 2 being the most potent.We thank the National Health and Medical Research Council, the Australian Research Council, and the Institute of Advanced Studies for financial support. J.N.B. is the grateful recipient of a Ph.D. Scholarship provided by the Australian Government. Dr. Hideki Onagi is thanked for assistance with chiral HPLC analyses. L.M.K. is a NH&MRC Australia Fellow.application/pdfen-AU© 2017 American Chemical Societyhttps://pubs.acs.org/page/policy/authorchoice_termsofuse.html201710.1021/acsomega.7b014592020-11-23ACS AuthorChoice License