Development of E-and Z-Selective Base-Catalyzed Redox Isomerizations and Ene-Diene Cross Metathesis
?-Oxo-?,?-alkenoates are found in several natural products and are versatile synthetic
intermediates. We have developed methods to selectively prepare E and Z-alkenoates from ?-hydroxy-?,?-alkynoates wherein the optimization, mechanism, and scope of the reactions are described. Biological testing of ?-oxo-?,?-alkenoates and their derivatives in zebrafish embryos also are discussed.
Since the development of ruthenium alkylidene catalysts, olefin metathesis has become a
useful method in synthetic organic chemistry. However, certain areas of metathesis have
remained under-researched; in particular, the cross metathesis of a 1,3-diene with a terminal
olefin known as ene-diene cross metathesis (EDCM). The attempt at optimization of EDCM
reactions using a general model is also discussed.
Advisor:Kazunori Koide; Christian E. Schafmeister; Paul E. Floreancig
School:University of Pittsburgh
School Location:USA - Pennsylvania
Source Type:Master's Thesis
Date of Publication:06/29/2006