Martin, Stephen F.1233555192008-08-282008-08-282006http://hdl.handle.net/2152/2709textA stereocontrolled approach to the elaborate skeleton of the solandelactone oxylipins culminating in the total synthesis of solandelactone E in 26 steps and 0.7% overall yield from commercially available D-glyceraldehyde acetonide has been successfully developed and executed. Highlights of the synthesis include a novel diastereoselective, acetal directed cyclopropanation of an electron deficient olefin, a diastereoselective asymmetric dihydroxylation, and a stereoselective [2, 3]-sigmatropic rearrangement of a chiral selenoxide intermediate. This innovative route can be easily adapted to gain access to other oxylipins of differing carboskeletal framework.electronicengCopyright is held by the author. Presentation of this material on the Libraries' web site by University Libraries, The University of Texas at Austin was made possible under a limited license grant from the author who has retained all copyrights in the works.Lactones--SynthesisThesis