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

[Image: see text] 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...

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Autores principales: Leitis, Zigma̅rs, Sakaine, Guna, Kine̅ns, Artis, Smits, Gints
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9434771/
https://www.ncbi.nlm.nih.gov/pubmed/36061714
http://dx.doi.org/10.1021/acsomega.2c03732
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author Leitis, Zigma̅rs
Sakaine, Guna
Kine̅ns, Artis
Smits, Gints
author_facet Leitis, Zigma̅rs
Sakaine, Guna
Kine̅ns, Artis
Smits, Gints
author_sort Leitis, Zigma̅rs
collection PubMed
description [Image: see text] 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.
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spelling pubmed-94347712022-09-02 Stereoselective Olefination with Sterically Demanding Julia–Kocienski Reagents: Total Synthesis of Oxo-prothracarcin, Oxo-tomaymycin, and Boseongazepine B Leitis, Zigma̅rs Sakaine, Guna Kine̅ns, Artis Smits, Gints ACS Omega [Image: see text] 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. American Chemical Society 2022-08-17 /pmc/articles/PMC9434771/ /pubmed/36061714 http://dx.doi.org/10.1021/acsomega.2c03732 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Leitis, Zigma̅rs
Sakaine, Guna
Kine̅ns, Artis
Smits, Gints
Stereoselective Olefination with Sterically Demanding Julia–Kocienski Reagents: Total Synthesis of Oxo-prothracarcin, Oxo-tomaymycin, and Boseongazepine B
title Stereoselective Olefination with Sterically Demanding Julia–Kocienski Reagents: Total Synthesis of Oxo-prothracarcin, Oxo-tomaymycin, and Boseongazepine B
title_full Stereoselective Olefination with Sterically Demanding Julia–Kocienski Reagents: Total Synthesis of Oxo-prothracarcin, Oxo-tomaymycin, and Boseongazepine B
title_fullStr Stereoselective Olefination with Sterically Demanding Julia–Kocienski Reagents: Total Synthesis of Oxo-prothracarcin, Oxo-tomaymycin, and Boseongazepine B
title_full_unstemmed Stereoselective Olefination with Sterically Demanding Julia–Kocienski Reagents: Total Synthesis of Oxo-prothracarcin, Oxo-tomaymycin, and Boseongazepine B
title_short Stereoselective Olefination with Sterically Demanding Julia–Kocienski Reagents: Total Synthesis of Oxo-prothracarcin, Oxo-tomaymycin, and Boseongazepine B
title_sort stereoselective olefination with sterically demanding julia–kocienski reagents: total synthesis of oxo-prothracarcin, oxo-tomaymycin, and boseongazepine b
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9434771/
https://www.ncbi.nlm.nih.gov/pubmed/36061714
http://dx.doi.org/10.1021/acsomega.2c03732
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