Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines

A one-flask, two-step procedure from 3-amino-2-methyl-5,6,7,7a-tetrahydro-1H-pyrrolizin-1-one affords the Streptomyces secondary metabolites legonmycins A and B – three operations overall from methyl N-Boc-prolinate. The key step proceeds in each case via N,O-diacylation, then selective oxidative hy...

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Detalles Bibliográficos
Autores principales: Lewis, Wilfred J M, Shaw, David M, Robertson, Jeremy
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2021
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7871033/
https://www.ncbi.nlm.nih.gov/pubmed/33828615
http://dx.doi.org/10.3762/bjoc.17.31
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author Lewis, Wilfred J M
Shaw, David M
Robertson, Jeremy
author_facet Lewis, Wilfred J M
Shaw, David M
Robertson, Jeremy
author_sort Lewis, Wilfred J M
collection PubMed
description A one-flask, two-step procedure from 3-amino-2-methyl-5,6,7,7a-tetrahydro-1H-pyrrolizin-1-one affords the Streptomyces secondary metabolites legonmycins A and B – three operations overall from methyl N-Boc-prolinate. The key step proceeds in each case via N,O-diacylation, then selective oxidative hydrolysis of the intermediate bicyclic pyrrole and establishes a precedent for the synthesis of related C(7a)-hydroxylated pyrrolizidines.
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spelling pubmed-78710332021-04-06 Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines Lewis, Wilfred J M Shaw, David M Robertson, Jeremy Beilstein J Org Chem Full Research Paper A one-flask, two-step procedure from 3-amino-2-methyl-5,6,7,7a-tetrahydro-1H-pyrrolizin-1-one affords the Streptomyces secondary metabolites legonmycins A and B – three operations overall from methyl N-Boc-prolinate. The key step proceeds in each case via N,O-diacylation, then selective oxidative hydrolysis of the intermediate bicyclic pyrrole and establishes a precedent for the synthesis of related C(7a)-hydroxylated pyrrolizidines. Beilstein-Institut 2021-02-02 /pmc/articles/PMC7871033/ /pubmed/33828615 http://dx.doi.org/10.3762/bjoc.17.31 Text en Copyright © 2021, Lewis et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/terms/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms)
spellingShingle Full Research Paper
Lewis, Wilfred J M
Shaw, David M
Robertson, Jeremy
Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines
title Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines
title_full Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines
title_fullStr Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines
title_full_unstemmed Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines
title_short Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines
title_sort synthesis of legonmycins a and b, c(7a)-hydroxylated bacterial pyrrolizidines
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7871033/
https://www.ncbi.nlm.nih.gov/pubmed/33828615
http://dx.doi.org/10.3762/bjoc.17.31
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