Total Synthesis and Structure Assignment of Saptomycin H

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.

Automated summary

The first total synthesis of saptomycin H is reported in this study, which allows the determination of the unidentified absolute stereochemistry of the oxiranyl side chain as 14R,16S. The key steps include the concise assembly of three units (anthrone, sugar, and side chain) and the AZADOL-mediated 6-endo-selective pyranone formation.