Fully Biocatalytic Rearrangement of Furans to Spirolactones

• Published in: ACS Catalysis
• Main Authors: Liu, Yu-Chang, Rolfes, J. D., Björklund, Joel, Deska, Jan
• Other Authors: Department of Chemistry and Materials Science, Bioorganic chemistry, Albert Hofmann Institute for Physiochemical Sustainability, Aalto-yliopisto, Aalto University
• Format: Article in Journal/Newspaper
• Language: English
• Published: American Chemical Society 2023
• Subjects: biocatalytic; cascade catalysis; cyclization; furans; multienzymatic; rearrangement; spirolactone; Heikkinen; Nils; sami
• Online Access: https://aaltodoc.aalto.fi/handle/123456789/121967; https://doi.org/10.1021/acscatal.3c00132

| openaire: EC/H2020/865885/EU//ABIONYS Funding Information: We gratefully acknowledge financial support of this study by the European Research Council (865885 (J.D.)), the Academy of Finland (298250 (J.D.) & 324854 (Y.C.L.)), the Ruth & Nils-Erik Stenbäcks Stiftelse (J.D.), and the Novo Nordisk Fonden (NNF17OC0025092 (Y.C.L.)). We also thank the Max-Planck-Institut für Kohlenforschung for the generous supply of computational resources and Sami Heikkinen for the assistance with the NMR spectroscopy. Publisher Copyright: © 2023 The Authors. Published by American Chemical Society. 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. Peer reviewed