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A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloids
This review relates all the results that we obtained in the field of the total synthesis of indolizidine and quinolizidine alkaloids using a strategy of the addition of an allylsilane on an N-acyliminium ion. In this paper, we describe the synthesis of racemic indolizidine 167B and chiral indolizidi...
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Formato: | Texto |
Lenguaje: | English |
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Beilstein-Institut
2007
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2148044/ https://www.ncbi.nlm.nih.gov/pubmed/17910752 http://dx.doi.org/10.1186/1860-5397-3-32 |
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author | Remuson, Roland |
author_facet | Remuson, Roland |
author_sort | Remuson, Roland |
collection | PubMed |
description | This review relates all the results that we obtained in the field of the total synthesis of indolizidine and quinolizidine alkaloids using a strategy of the addition of an allylsilane on an N-acyliminium ion. In this paper, we describe the synthesis of racemic indolizidine 167B and chiral indolizidines: (-)-indolizidines 167B, 195B, 223AB, (+)-monomorine, (-)-(3R,5S,8aS)-3-butyl-5-propylindolizidine and (-)-dendroprimine. Next, we relate the synthesis that we have developed in the quinolizidines field: (±)-myrtine and epimyrtine, (±)-lasubines I and II and chiral quinolizidines: (+)-myrtine, (-)-epimyrtine, (-)-lasubines I and II and (+)-subcosine II. |
format | Text |
id | pubmed-2148044 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2007 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-21480442007-12-20 A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloids Remuson, Roland Beilstein J Org Chem Review This review relates all the results that we obtained in the field of the total synthesis of indolizidine and quinolizidine alkaloids using a strategy of the addition of an allylsilane on an N-acyliminium ion. In this paper, we describe the synthesis of racemic indolizidine 167B and chiral indolizidines: (-)-indolizidines 167B, 195B, 223AB, (+)-monomorine, (-)-(3R,5S,8aS)-3-butyl-5-propylindolizidine and (-)-dendroprimine. Next, we relate the synthesis that we have developed in the quinolizidines field: (±)-myrtine and epimyrtine, (±)-lasubines I and II and chiral quinolizidines: (+)-myrtine, (-)-epimyrtine, (-)-lasubines I and II and (+)-subcosine II. Beilstein-Institut 2007-10-02 /pmc/articles/PMC2148044/ /pubmed/17910752 http://dx.doi.org/10.1186/1860-5397-3-32 Text en Copyright © 2007, Remuson 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 | Review Remuson, Roland A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloids |
title | A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloids |
title_full | A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloids |
title_fullStr | A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloids |
title_full_unstemmed | A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloids |
title_short | A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloids |
title_sort | convenient allylsilane-n-acyliminium route toward indolizidine and quinolizidine alkaloids |
topic | Review |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2148044/ https://www.ncbi.nlm.nih.gov/pubmed/17910752 http://dx.doi.org/10.1186/1860-5397-3-32 |
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