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The enantiospecific synthesis of (+)-monomorine I using a 5-endo-trig cyclisation strategy
We have developed a general strategy for the synthesis of 2,5-syn disubstituted pyrrolidines that is based on the multi-faceted reactivity of the sulfone moiety and a 5-endo-trig cyclisation. This methodology was applied to the synthesis of indolizidine alkaloid monomorine I. Two factors were key to...
Autores principales: | , , , |
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Formato: | Texto |
Lenguaje: | English |
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Beilstein-Institut
2007
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2151076/ https://www.ncbi.nlm.nih.gov/pubmed/17996034 http://dx.doi.org/10.1186/1860-5397-3-39 |
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author | Berry, Malcolm B Craig, Donald Jones, Philip S Rowlands, Gareth J |
author_facet | Berry, Malcolm B Craig, Donald Jones, Philip S Rowlands, Gareth J |
author_sort | Berry, Malcolm B |
collection | PubMed |
description | We have developed a general strategy for the synthesis of 2,5-syn disubstituted pyrrolidines that is based on the multi-faceted reactivity of the sulfone moiety and a 5-endo-trig cyclisation. This methodology was applied to the synthesis of indolizidine alkaloid monomorine I. Two factors were key to the success of this endeavour; the first was the choice of nitrogen protecting group whilst the second was the conditions for the final stereoselective amination step. Employing a combination of different protecting groups and an intramolecular reductive amination reaction we were able to prepare (+)-monomorine I in just 11 steps from commercially available D-norleucine in a completely stereoselective manner. |
format | Text |
id | pubmed-2151076 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2007 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-21510762007-12-21 The enantiospecific synthesis of (+)-monomorine I using a 5-endo-trig cyclisation strategy Berry, Malcolm B Craig, Donald Jones, Philip S Rowlands, Gareth J Beilstein J Org Chem Full Research Paper We have developed a general strategy for the synthesis of 2,5-syn disubstituted pyrrolidines that is based on the multi-faceted reactivity of the sulfone moiety and a 5-endo-trig cyclisation. This methodology was applied to the synthesis of indolizidine alkaloid monomorine I. Two factors were key to the success of this endeavour; the first was the choice of nitrogen protecting group whilst the second was the conditions for the final stereoselective amination step. Employing a combination of different protecting groups and an intramolecular reductive amination reaction we were able to prepare (+)-monomorine I in just 11 steps from commercially available D-norleucine in a completely stereoselective manner. Beilstein-Institut 2007-11-08 /pmc/articles/PMC2151076/ /pubmed/17996034 http://dx.doi.org/10.1186/1860-5397-3-39 Text en Copyright © 2007, Berry et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Full Research Paper Berry, Malcolm B Craig, Donald Jones, Philip S Rowlands, Gareth J The enantiospecific synthesis of (+)-monomorine I using a 5-endo-trig cyclisation strategy |
title | The enantiospecific synthesis of (+)-monomorine I using a 5-endo-trig cyclisation strategy |
title_full | The enantiospecific synthesis of (+)-monomorine I using a 5-endo-trig cyclisation strategy |
title_fullStr | The enantiospecific synthesis of (+)-monomorine I using a 5-endo-trig cyclisation strategy |
title_full_unstemmed | The enantiospecific synthesis of (+)-monomorine I using a 5-endo-trig cyclisation strategy |
title_short | The enantiospecific synthesis of (+)-monomorine I using a 5-endo-trig cyclisation strategy |
title_sort | enantiospecific synthesis of (+)-monomorine i using a 5-endo-trig cyclisation strategy |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2151076/ https://www.ncbi.nlm.nih.gov/pubmed/17996034 http://dx.doi.org/10.1186/1860-5397-3-39 |
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