Elucidation of the regio- and chemoselectivity of enzymatic allylic oxidations with Pleurotus sapidus - conversion of selected spirocyclic terpenoids and computational analysis.

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

SUBMITTER: Weidmann V 

PROVIDER: S-EPMC3817473 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature