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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The 3-Hydroxycineoles

Raymond M. Carman A C , Ward T. Robinson B and Craig J. Wallis A
+ Author Affiliations
- Author Affiliations

A Chemistry, University of Queensland, Brisbane QLD 4072, Australia.

B Department of Chemistry, University of Canterbury, Christchurch, New Zealand.

C Corresponding author. Email: carman@chemistry.uq.edu.au

Australian Journal of Chemistry 58(11) 785-791 https://doi.org/10.1071/CH05144
Submitted: 20 June 2005  Accepted: 21 September 2005   Published: 9 December 2005

Abstract

Data concerning the 3-hydroxycineoles 1 and 2 are provided to enable the ready identification of these metabolites and to determine their enantiomeric excess in mixtures. An unusual SN2-type inversion at a tertiary center is observed during one synthetic approach.


Acknowledgment

We thank Tommy Karoli for early investigations into these systems.


References


[1]   H. Nishimura, Y. Noma, J. Mizutani, J. Agric. Biol. Chem. 1982, 46,  2601.
         
         
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* We thank a referee for discussion on this point.