Issue 28, 2024

Enantioselective synthesis of all stereoisomers of geosmin and of biosynthetically related natural products

Abstract

Synthetic routes to geosmin and its enantiomer are well established, but the enantioselective synthesis of stereoisomers of geosmin is unknown. Here a stereoselective synthesis of all stereoisomers of geosmin is reported, yielding all compounds in high enantiomeric purity. Furthermore, the stereoselective synthesis of a geosmin derivative isolated from a mangrove associated streptomycete was performed, establishing the absolute configuration of the natural product. Finally, a new side product of the geosmin synthase from Streptomyces ambofaciens was isolated and its structure was elucidated by NMR spectroscopy. The absolute configuration of this new compound was determined through a stereoselective synthesis.

Graphical abstract: Enantioselective synthesis of all stereoisomers of geosmin and of biosynthetically related natural products

Supplementary files

Article information

Article type
Paper
Submitted
03 Jun 2024
Accepted
21 Jun 2024
First published
24 Jun 2024

Org. Biomol. Chem., 2024,22, 5748-5758

Enantioselective synthesis of all stereoisomers of geosmin and of biosynthetically related natural products

Z. Yin, M. Maczka, G. Schnakenburg, S. Schulz and J. S. Dickschat, Org. Biomol. Chem., 2024, 22, 5748 DOI: 10.1039/D4OB00934G

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