Total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A via late-stage nickel-catalyzed cross coupling

The first total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A have been accomplished using a nickel-catalyzed cross coupling of alkyl bromide with vinyl stannane as the final step. The other key steps include late-stage C(sp(3))–H bromination, the...

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Autores principales: Wang, Hengtao, Zhang, Xiunan, Tang, Pingping
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5633787/
https://www.ncbi.nlm.nih.gov/pubmed/29081957
http://dx.doi.org/10.1039/c7sc03293e
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author Wang, Hengtao
Zhang, Xiunan
Tang, Pingping
author_facet Wang, Hengtao
Zhang, Xiunan
Tang, Pingping
author_sort Wang, Hengtao
collection PubMed
description The first total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A have been accomplished using a nickel-catalyzed cross coupling of alkyl bromide with vinyl stannane as the final step. The other key steps include late-stage C(sp(3))–H bromination, the oxidative cleavage of a diol to provide the requisite ketone and ester for schilancidilactones A and B, and Dieckmann-type condensation to generate the A ring of schilancitrilactone A and 20-epi-schilancitrilactone A.
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spelling pubmed-56337872017-10-27 Total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A via late-stage nickel-catalyzed cross coupling Wang, Hengtao Zhang, Xiunan Tang, Pingping Chem Sci Chemistry The first total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A have been accomplished using a nickel-catalyzed cross coupling of alkyl bromide with vinyl stannane as the final step. The other key steps include late-stage C(sp(3))–H bromination, the oxidative cleavage of a diol to provide the requisite ketone and ester for schilancidilactones A and B, and Dieckmann-type condensation to generate the A ring of schilancitrilactone A and 20-epi-schilancitrilactone A. Royal Society of Chemistry 2017-10-01 2017-08-30 /pmc/articles/PMC5633787/ /pubmed/29081957 http://dx.doi.org/10.1039/c7sc03293e Text en This journal is © The Royal Society of Chemistry 2017 http://creativecommons.org/licenses/by-nc/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial 3.0 Unported License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Wang, Hengtao
Zhang, Xiunan
Tang, Pingping
Total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A via late-stage nickel-catalyzed cross coupling
title Total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A via late-stage nickel-catalyzed cross coupling
title_full Total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A via late-stage nickel-catalyzed cross coupling
title_fullStr Total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A via late-stage nickel-catalyzed cross coupling
title_full_unstemmed Total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A via late-stage nickel-catalyzed cross coupling
title_short Total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A via late-stage nickel-catalyzed cross coupling
title_sort total syntheses of schilancidilactones a and b, schilancitrilactone a, and 20-epi-schilancitrilactone a via late-stage nickel-catalyzed cross coupling
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5633787/
https://www.ncbi.nlm.nih.gov/pubmed/29081957
http://dx.doi.org/10.1039/c7sc03293e
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AT zhangxiunan totalsynthesesofschilancidilactonesaandbschilancitrilactoneaand20epischilancitrilactoneavialatestagenickelcatalyzedcrosscoupling
AT tangpingping totalsynthesesofschilancidilactonesaandbschilancitrilactoneaand20epischilancitrilactoneavialatestagenickelcatalyzedcrosscoupling

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