Stereoselective Olefination with Sterically Demanding Julia-Kocienski Reagents: Total Synthesis of Oxo-prothracarcin, Oxo-tomaymycin, and Boseongazepine B.
| Autor: | Leitis ZR; Latvian Institute of Organic Synthesis, Aizkraukles str. 21, Riga LV-1006, Latvia., Sakaine G; Latvian Institute of Organic Synthesis, Aizkraukles str. 21, Riga LV-1006, Latvia., Kine Ns A; Latvian Institute of Organic Synthesis, Aizkraukles str. 21, Riga LV-1006, Latvia.; Department of Chemistry, University of Latvia, Jelgavas str. 1, Riga LV-1004, Latvia., Smits G; Latvian Institute of Organic Synthesis, Aizkraukles str. 21, Riga LV-1006, Latvia. |
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| Jazyk: | angličtina |
| Zdroj: | ACS omega [ACS Omega] 2022 Aug 17; Vol. 7 (34), pp. 30519-30534. Date of Electronic Publication: 2022 Aug 17 (Print Publication: 2022). |
| DOI: | 10.1021/acsomega.2c03732 |
| Abstrakt: | 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. Competing Interests: The authors declare no competing financial interest. (© 2022 The Authors. Published by American Chemical Society.) |
| Databáze: | MEDLINE |
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