Journal article

Publication year: 2013

Pages: 2233-2241

Journal: Beilstein Journal of Organic Chemistry

Volume number: 9

ISSN: 1860-5397

Open access status: Gold

DOI Link: https://doi.org/10.3762/bjoc.9.262

Publisher: Beilstein-Institut

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.

Harvard Citation style: Weidmann, V., Schaffrath, M., Zorn, H., Rehbein, J. and Maison, W. (2013) Elucidation of the regio- and chemoselectivity of enzymatic allylic oxidations with Pleurotus sapidus - conversion of selected spirocyclic terpenoids and computational analysis, Beilstein Journal of Organic Chemistry, 9, pp. 2233-2241. https://doi.org/10.3762/bjoc.9.262

APA Citation style: Weidmann, V., Schaffrath, M., Zorn, H., Rehbein, J., & Maison, W. (2013). Elucidation of the regio- and chemoselectivity of enzymatic allylic oxidations with Pleurotus sapidus - conversion of selected spirocyclic terpenoids and computational analysis. Beilstein Journal of Organic Chemistry. 9, 2233-2241. https://doi.org/10.3762/bjoc.9.262