Total Synthesis and Structure Assignment of Saptomycin H

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Abstract

We report herein the first total synthesis of saptomycin H (2), by which the unidentified absolute stereochemistry of the oxiranyl side chain has been determined as 14R,16S. The keys include (1) concise assembly of three units, anthrone, sugar and side chain, and (2) AZADOL-mediated 6-endo-selective pyranone (A-ring) formation.

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Shimura, J., Ando, Y., Ohmori, K., & Suzuki, K. (2022). Total Synthesis and Structure Assignment of Saptomycin H. Organic Letters, 24(7), 1439–1443. https://doi.org/10.1021/acs.orglett.1c04306

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