Absolute Configurations of Naturally Occurring Quinones: Ventilagone and Dunnione
Raymond G. Cooke A * , Emilio L. Ghisalberti B C , Brian L. Johnson A B , Colin L. Raston B , Brian W. Skelton B and Allan H. White BA Department of Organic Chemistry, University of Melbourne, Parkville VIC 3052, Australia.
B Chemistry M313, School of Biomedical, Biomolecular and Chemical Sciences, University of Western Australia, Crawley WA 6009, Australia.
C Corresponding author. Email: elg@chem.uwa.edu.au
Australian Journal of Chemistry 59(12) 925-930 https://doi.org/10.1071/CH06365
Submitted: 10 October 2006 Accepted: 6 November 2006 Published: 20 December 2006
Abstract
Low-temperature determinations of the crystal structures of the naturally occurring quinones ventilagone (as its p-bromobenzyl ether) and dunnione (as its p-bromophenylhydrazone) permit the assignment of their absolute configurations as (1R,3S)-7,10-dihydroxy-1,3,8-trimethyl-3,4,6,9-tetrahydro-1H-naphtho[2,3-c]-pyrane-6,9-dione 1 and (2R)-2,3-dihydro-2,3,3-trimethylnaphtho[1,2-b]furan-4,5-dione 2.
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* Deceased.
