Application of Lithiation–Borylation to the Total Synthesis of (−)-Rakicidin F

[Image: see text] The stereochemistry of the lipophilic side chain of (+)-rakicidin F had not been determined until recently. Using our lithiation–borylation methodology (“assembly line synthesis”) we were able to efficiently prepare the all-syn isomer as well as the C-21 epimer of the side chain, a...

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Autores principales: Bold, Christian P., Yeung, Kay, Pape, Felix, Kaiser, Daniel, Aggarwal, Varinder K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9806854/
https://www.ncbi.nlm.nih.gov/pubmed/36538642
http://dx.doi.org/10.1021/acs.orglett.2c03716
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author Bold, Christian P.
Yeung, Kay
Pape, Felix
Kaiser, Daniel
Aggarwal, Varinder K.
author_facet Bold, Christian P.
Yeung, Kay
Pape, Felix
Kaiser, Daniel
Aggarwal, Varinder K.
author_sort Bold, Christian P.
collection PubMed
description [Image: see text] The stereochemistry of the lipophilic side chain of (+)-rakicidin F had not been determined until recently. Using our lithiation–borylation methodology (“assembly line synthesis”) we were able to efficiently prepare the all-syn isomer as well as the C-21 epimer of the side chain, and comparison with the natural product suggested that the natural product had all-syn stereochemistry. Completion of the total synthesis using a macrolactamization of the northern amide enabled us to confirm Wang and Chen’s stereochemical findings for the structure of (+)-rakicidin F.
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spelling pubmed-98068542023-01-03 Application of Lithiation–Borylation to the Total Synthesis of (−)-Rakicidin F Bold, Christian P. Yeung, Kay Pape, Felix Kaiser, Daniel Aggarwal, Varinder K. Org Lett [Image: see text] The stereochemistry of the lipophilic side chain of (+)-rakicidin F had not been determined until recently. Using our lithiation–borylation methodology (“assembly line synthesis”) we were able to efficiently prepare the all-syn isomer as well as the C-21 epimer of the side chain, and comparison with the natural product suggested that the natural product had all-syn stereochemistry. Completion of the total synthesis using a macrolactamization of the northern amide enabled us to confirm Wang and Chen’s stereochemical findings for the structure of (+)-rakicidin F. American Chemical Society 2022-12-20 2022-12-30 /pmc/articles/PMC9806854/ /pubmed/36538642 http://dx.doi.org/10.1021/acs.orglett.2c03716 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Bold, Christian P.
Yeung, Kay
Pape, Felix
Kaiser, Daniel
Aggarwal, Varinder K.
Application of Lithiation–Borylation to the Total Synthesis of (−)-Rakicidin F
title Application of Lithiation–Borylation to the Total Synthesis of (−)-Rakicidin F
title_full Application of Lithiation–Borylation to the Total Synthesis of (−)-Rakicidin F
title_fullStr Application of Lithiation–Borylation to the Total Synthesis of (−)-Rakicidin F
title_full_unstemmed Application of Lithiation–Borylation to the Total Synthesis of (−)-Rakicidin F
title_short Application of Lithiation–Borylation to the Total Synthesis of (−)-Rakicidin F
title_sort application of lithiation–borylation to the total synthesis of (−)-rakicidin f
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9806854/
https://www.ncbi.nlm.nih.gov/pubmed/36538642
http://dx.doi.org/10.1021/acs.orglett.2c03716
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