Fully Biocatalytic Rearrangement of Furans to Spirolactones
Yu-Chang Liu1,2, J D Rolfes3, Joel Björklund2
1Department of Chemistry, University of Helsinki, A.I. Virtasen aukio 1, 00560 Helsinki, Finland.
Abstract:
A multienzymatic pathway enables the preparation of optically pure spirolactone building blocks. In a streamlined one-pot reaction cascade, the combination of chloroperoxidase, an oxidase, and an alcohol dehydrogenase renders an efficient reaction cascade for the conversion of hydroxy-functionalized furans to the spirocyclic products. The fully biocatalytic method is successfully employed in the total synthesis of the bioactive natural product (+)-crassalactone D, and as the key module in a chemoenzymatic route yielding lanceolactone A.
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