Date of Award
Doctor of Philosophy
It was the purpose of this thesis work to develop new cyclization sequences to be used toward the synthesis of various carbocyclic terpenes. Three such sequences were discovered;One sequence dealt with the 1,4-conjugate addition of various furans to certain cyclic enones mediated by iodotrimethylsilane;Another sequence utilized the same general reaction except that dienol silyl ethers were employed instead of furans to yield bicyclic and tricyclic compounds. These compounds would be useful for the synthesis of several diterpene analogues such as the steroids or the quassinoids;The final sequence dealt with (beta)-hydroxy-(gamma)-lactone synthesis. This was done with the novel reagent bromo-acetaldehyde which we were able to produce in anhydrous form. We have ultimately improved the reaction sequence to entail a one-pot procedure resulting in good yields of the desired products. Such products could be used toward the synthesis of naturally occurring (beta)-hydroxy-(gamma)-lactones such as the litsolenolides.
Digital Repository @ Iowa State University, http://lib.dr.iastate.edu/
Gottschalk, Peter, "New strategies in the synthesis of carbocyclic natural products " (1983). Retrospective Theses and Dissertations. 8472.