A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloids

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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Main Author: Roland Remuson
Format: Article
Language:English
Published: Beilstein-Institut 2007-10-01
Series:Beilstein Journal of Organic Chemistry
Online Access:https://doi.org/10.1186/1860-5397-3-32
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spelling doaj-ce0392cfc77a48358e517d73ed98f4c72021-04-02T07:13:29ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972007-10-01313210.1186/1860-5397-3-321860-5397-3-32A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloidsRoland Remuson0UMR 6504, CNRS Université Blaise Pascal (Clermont-Fd), 63177 Aubière Cédex, FranceThis 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.https://doi.org/10.1186/1860-5397-3-32
collection DOAJ
language English
format Article
sources DOAJ
author Roland Remuson
spellingShingle Roland Remuson
A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloids
Beilstein Journal of Organic Chemistry
author_facet Roland Remuson
author_sort Roland Remuson
title 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_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_sort convenient allylsilane-n-acyliminium route toward indolizidine and quinolizidine alkaloids
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2007-10-01
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.
url https://doi.org/10.1186/1860-5397-3-32
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AT rolandremuson convenientallylsilanenacyliminiumroutetowardindolizidineandquinolizidinealkaloids
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