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Molecules 2013, 18(3), 2778-2787; doi:10.3390/molecules18032778
Article

Lactones 41. Synthesis and Microbial Hydroxylation of Unsaturated Terpenoid Lactones with p-Menthane Ring Systems

*  and
Department of Chemistry, Faculty of Food Science, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland
This paper is the 41th part of our series of Lactones papers.
* Author to whom correspondence should be addressed.
Received: 29 January 2013 / Revised: 20 February 2013 / Accepted: 21 February 2013 / Published: 1 March 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

Racemic [(±)-4-isopropyl-1-methyl-7-oxa-cis-bicyclo[4.3.0]non-4-en-8-one] and optically active d,e-unsaturated lactones [(-)-(1R,6R)-4-isopropyl-1-methyl-7-oxabicyclo[4.3.0]non-4-en-8-one and (+)-(1S,6S)-4-isopropyl-1-methyl-7-oxabicyclo[4.3.0] non-4-en-8-one)] with the p-menthane system were obtained and their odoriferous properties were evaluated. Biotransformations of the racemic lactone with three fungal strains: Absidia cylindrospora AM336, Absidia glauca AM177 and Syncephalastrum racemosum AM105, were carried out. Microbial transformations afforded hydroxylactones with the hydroxy group in the allylic position.
Keywords: lactones; p-menthane system; biotransformation; hydroxylation; odoriferous compounds; Absidia cylindrospora; Absidia glauca; Syncephalastrum racemosum lactones; p-menthane system; biotransformation; hydroxylation; odoriferous compounds; Absidia cylindrospora; Absidia glauca; Syncephalastrum racemosum
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Grudniewska, A.; Wawrzeńczyk, C. Lactones 41. Synthesis and Microbial Hydroxylation of Unsaturated Terpenoid Lactones with p-Menthane Ring Systems. Molecules 2013, 18, 2778-2787.

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