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

ACS Omega 2022
Zigmārs Leitis, Guna Sakaine, Artis Kinēns, Gints Šmits

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.

Keywords
Ireland-Claisen Rearrangement, Cytotoxicity
DOI
10.1021/acsomega.2c03732
Hyperlink
https://pubs.acs.org/doi/10.1021/acsomega.2c03732

Leitis, Z., Sakaine, G., Kinēns, A., Šmits, G. Stereoselective Olefination with Sterically Demanding Julia-Kocienski Reagents: Total Synthesis of Oxo-prothracarcin, Oxo-tomaymycin, and Boseongazepine B. ACS Omega, 2022, Vol. 7, No. 34, pp.30519-30534. e-ISSN 2470-1343. Available from: doi:10.1021/acsomega.2c03732

Publication language
English (en)