Stereoselective Olefination with Sterically Demanding Julia–Kocienski Reagents: Total Synthesis of Oxo-prothracarcin, Oxo-tomaymycin, and Boseongazepine B

Total syntheses of three pyrrolo­[1,4]­benzodiazepine anticancer antibiotic family members oxo-prothracarcin, oxo-tomaymycin, and boseongazepine B are described. The total syntheses feature late-stage stereoselective olefination employing modified Julia–Kocienski reagents that can be conveniently pr...

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Bibliographic Details
Published in:ACS omega 2022-08, Vol.7 (34), p.30519-30534
Main Authors: Leitis, Zigma̅rs, Sakaine, Guna, Kine̅ns, Artis, Smits, Gints
Format: Article
Language:English
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Summary:Total syntheses of three pyrrolo­[1,4]­benzodiazepine anticancer antibiotic family members oxo-prothracarcin, oxo-tomaymycin, and boseongazepine B are described. The total syntheses feature late-stage stereoselective olefination employing modified Julia–Kocienski reagents that can be conveniently prepared in only two steps and allows for a significant reduction in the number of linear steps. Detailed density functional theory (DFT) studies explain the stereochemical outcome of the key step.
ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.2c03732