A Chemoenzymatic and Enantioselective Route to the Tricyclic Frameworks Associated with the Protoilludane and Marasmane Classes of Sesquiterpene
Date
2004
Authors
Banwell, Martin
Harfoot, Gwion
Journal Title
Journal ISSN
Volume Title
Publisher
CSIRO Publishing
Abstract
The enantiomerically pure cis-1,2-dihydrocatechol 3, which is obtained in quantity by microbial dihydroxylation of toluene, has been converted over ten steps, including an initial Diels-Alder cycloaddition reaction, into the tricyclic ketone 12. Direct irradiation of a benzene solution of the latter compound affords a mixture of compounds 13 and 14 which embody the tricyclic frameworks of the sesquiterpene natural products tsugicoline A (1) and isovelleral (2), respectively.
Description
Keywords
Keywords: Benzene; Escherichia coli; Genetic engineering; Irradiation; Mixtures; Synthesis (chemical); Toluene; Antibacterial properties; Chemical defense mechanisms; Enantiomers; Microbial dihydroxylation; Enzyme kinetics
Citation
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Source
Australian Journal of Chemistry
Type
Journal article