Stereochemistry and Mechanism of the Enzyme -Catalyzed Cyclizations of Farnesyl Diphosphate to the Sesquiterpenes Epi -Aristolochene, Epi-Eremophilene and Vetispiradiene

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.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2000

Author dc:creator

• Schenk, David John

Contributors dc:contributor

• Coates, Robert M.

• Chemistry, Biochemistry

Language dc:language

eng

Identifier

(MiAaPQ)AAI9990130

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/84497