Studies on the Stereochemistry and Mechanism of Taxadiene Biosynthesis
Jin, Qingwu
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Permalink
https://hdl.handle.net/2142/84445
Description
Title
Studies on the Stereochemistry and Mechanism of Taxadiene Biosynthesis
Author(s)
Jin, Qingwu
Issue Date
1999
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, Organic
Language
eng
Abstract
Enzyme-mediated cyclization of GPP, FPP, and GGPP goes through various carbocationic intermediates, and methoxy analogs of these substrates would provide strong stabilization towards the carbocation intermediates. Upon release from the enzyme, the non-natural products would provide valuable insights to the enzyme mechanisms that would otherwise be unavailable. Methoxy-substituted nor analogs of geraniol, farnesol, and geranylgeraniol were prepared by alkylation of carbanions generated from allylic ethers.
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