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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
Received: 29 January 2013; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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

AMA Style

Grudniewska A, Wawrzeńczyk C. Lactones 41. Synthesis and Microbial Hydroxylation of Unsaturated Terpenoid Lactones with p-Menthane Ring Systems. Molecules. 2013; 18(3):2778-2787.

Chicago/Turabian Style

Grudniewska, Aleksandra; Wawrzeńczyk, Czesław. 2013. "Lactones 41. Synthesis and Microbial Hydroxylation of Unsaturated Terpenoid Lactones with p-Menthane Ring Systems." Molecules 18, no. 3: 2778-2787.


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