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Elucidation of the regio- and chemoselectivity of enzymatic allylic oxidations with Pleurotus sapidus – conversion of selected spirocyclic terpenoids and computational analysis
- Source :
- Beilstein Journal of Organic Chemistry, Vol 9, Iss 1, Pp 2233-2241 (2013)
- Publication Year :
- 2013
- Publisher :
- Beilstein-Institut, 2013.
-
Abstract
- Allylic oxidations of olefins to enones allow the efficient synthesis of value-added products from simple olefinic precursors like terpenes or terpenoids. Biocatalytic variants have a large potential for industrial applications, particularly in the pharmaceutical and food industry. Herein we report efficient biocatalytic allylic oxidations of spirocyclic terpenoids by a lyophilisate of the edible fungus Pleurotus sapidus. This ‘’mushroom catalysis’’ is operationally simple and allows the conversion of various unsaturated spirocyclic terpenoids. A number of new spirocyclic enones have thus been obtained with good regio- and chemoselectivity and chiral separation protocols for enantiomeric mixtures have been developed. The oxidations follow a radical mechanism and the regioselectivity of the reaction is mainly determined by bond-dissociation energies of the available allylic CH-bonds and steric accessibility of the oxidation site.
Details
- Language :
- English
- ISSN :
- 18605397
- Volume :
- 9
- Issue :
- 1
- Database :
- Directory of Open Access Journals
- Journal :
- Beilstein Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- edsdoj.83c1627777364abd96d18198539e20e2
- Document Type :
- article
- Full Text :
- https://doi.org/10.3762/bjoc.9.262