Stereochemistry and Mechanism of the Enzyme -Catalyzed Cyclizations of Farnesyl Diphosphate to the Sesquiterpenes Epi -Aristolochene, Epi-Eremophilene and Vetispiradiene
Schenk, David John
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https://hdl.handle.net/2142/84497
Description
Title
Stereochemistry and Mechanism of the Enzyme -Catalyzed Cyclizations of Farnesyl Diphosphate to the Sesquiterpenes Epi -Aristolochene, Epi-Eremophilene and Vetispiradiene
Author(s)
Schenk, David John
Issue Date
2000
Doctoral Committee Chair(s)
Coates, Robert M.
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Biochemistry
Language
eng
Abstract
Chiral methyl FPPs were prepared by the displacement of allylic monodeuterated diethyl phosphates with LiBEt3T. (12R)- and ( 12S)-[12-2H1, 12-3H 1]FPPs were incubated with TEAS, and the 3H NMR spectra showed that several tritiated compounds were present. The facial selectivity of the proton elimination at the cis terminal could not be determined because of low radiochemical purity.
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