A Chemoenzymatic and Enantioselective Route to the Tricyclic Frameworks Associated with the Protoilludane and Marasmane Classes of Sesquiterpene
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.
|Collections||ANU Research Publications|
|Source:||Australian Journal of Chemistry|