A Chemoenzymatic and Enantioselective Route to the Tricyclic Frameworks Associated with the Protoilludane and Marasmane Classes of Sesquiterpene

Martin G. Banwell; Gwion J. Harfoot

doi:10.1071/CH04131

RESEARCH ARTICLE

Previous Contents Vol 57(9)

A Chemoenzymatic and Enantioselective Route to the Tricyclic Frameworks Associated with the Protoilludane and Marasmane Classes of Sesquiterpene

Martin G. Banwell ^A ^B and Gwion J. Harfoot ^A

+ Author Affiliations

- Author Affiliations

^A Research School of Chemistry, Institute of Advanced Studies, Australian National University, Canberra ACT 0200, Australia.

^B Author to whom correspondence should be addressed (e-mail: mgb@rsc.anu.edu.au).

Australian Journal of Chemistry 57(9) 895-897 https://doi.org/10.1071/CH04131
Submitted: 13 May 2004 Accepted: 30 June 2004 Published: 1 September 2004

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.

Acknowledgements

We thank Dr Gregg Whited (Genencor International Inc., Palo Alto, CA) and Professor T. Hudlicky (Brock University) for continued encouragement and the provision of generous quantities of cis-1,2-dihydrocatechol 3. G.J.H. is the grateful recipient of an APA and various supplementary scholarships that have supported him during the course of his Ph.D. studies.

References

A Chemoenzymatic and Enantioselective Route to the Tricyclic Frameworks Associated with the Protoilludane and Marasmane Classes of Sesquiterpene

Abstract

Acknowledgements

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