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Total synthesis of atropisomeric indolosesquiterpenoids via N–N bond formation: dixiamycins A and B
N–N dimeric indolosesquiterpene alkaloids constitute a class of under-investigated architecturally intriguing natural products. Herein, we report the first chemical oxidation approach to the asymmetric total syntheses of these atropisomeric indolosesquiterpenoids through N–N bond formation. Specific...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10395272/ https://www.ncbi.nlm.nih.gov/pubmed/37538818 http://dx.doi.org/10.1039/d2sc07119c |
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author | Nandi, Rhituparna Niyogi, Sovan Kundu, Sourav Gavit, Vipin R. Munda, Mintu Murmu, Ranjit Bisai, Alakesh |
author_facet | Nandi, Rhituparna Niyogi, Sovan Kundu, Sourav Gavit, Vipin R. Munda, Mintu Murmu, Ranjit Bisai, Alakesh |
author_sort | Nandi, Rhituparna |
collection | PubMed |
description | N–N dimeric indolosesquiterpene alkaloids constitute a class of under-investigated architecturally intriguing natural products. Herein, we report the first chemical oxidation approach to the asymmetric total syntheses of these atropisomeric indolosesquiterpenoids through N–N bond formation. Specifically, dixiamycins A (1a) and B (1b) were prepared through a Cu(i)-mediated aerobic dehydrogenative dimerization from the naturally occurring monomer xiamycin A methyl ester (2b); this preparation also represents the first total synthesis of dixiamycin A (1a). The monomer xiamycin A methyl ester (2b) was synthesized via a late-stage Buchwald Pd(ii)-mediated aerobic dehydrogenative C–N bond formation. |
format | Online Article Text |
id | pubmed-10395272 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-103952722023-08-03 Total synthesis of atropisomeric indolosesquiterpenoids via N–N bond formation: dixiamycins A and B Nandi, Rhituparna Niyogi, Sovan Kundu, Sourav Gavit, Vipin R. Munda, Mintu Murmu, Ranjit Bisai, Alakesh Chem Sci Chemistry N–N dimeric indolosesquiterpene alkaloids constitute a class of under-investigated architecturally intriguing natural products. Herein, we report the first chemical oxidation approach to the asymmetric total syntheses of these atropisomeric indolosesquiterpenoids through N–N bond formation. Specifically, dixiamycins A (1a) and B (1b) were prepared through a Cu(i)-mediated aerobic dehydrogenative dimerization from the naturally occurring monomer xiamycin A methyl ester (2b); this preparation also represents the first total synthesis of dixiamycin A (1a). The monomer xiamycin A methyl ester (2b) was synthesized via a late-stage Buchwald Pd(ii)-mediated aerobic dehydrogenative C–N bond formation. The Royal Society of Chemistry 2023-06-20 /pmc/articles/PMC10395272/ /pubmed/37538818 http://dx.doi.org/10.1039/d2sc07119c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Nandi, Rhituparna Niyogi, Sovan Kundu, Sourav Gavit, Vipin R. Munda, Mintu Murmu, Ranjit Bisai, Alakesh Total synthesis of atropisomeric indolosesquiterpenoids via N–N bond formation: dixiamycins A and B |
title | Total synthesis of atropisomeric indolosesquiterpenoids via N–N bond formation: dixiamycins A and B |
title_full | Total synthesis of atropisomeric indolosesquiterpenoids via N–N bond formation: dixiamycins A and B |
title_fullStr | Total synthesis of atropisomeric indolosesquiterpenoids via N–N bond formation: dixiamycins A and B |
title_full_unstemmed | Total synthesis of atropisomeric indolosesquiterpenoids via N–N bond formation: dixiamycins A and B |
title_short | Total synthesis of atropisomeric indolosesquiterpenoids via N–N bond formation: dixiamycins A and B |
title_sort | total synthesis of atropisomeric indolosesquiterpenoids via n–n bond formation: dixiamycins a and b |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10395272/ https://www.ncbi.nlm.nih.gov/pubmed/37538818 http://dx.doi.org/10.1039/d2sc07119c |
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