The 5-Endo-trig Cyclization of d-Glucose Derived γ-Alkenylamines with Mercury (II) Salts: Synthesis of 1-Deoxy-castanospermine and its 8a-epi-Analogue†

The intramolecular aminomercuration of γ-alkenylamines 1a, 1b and 4 was shown to afford the 5-endo-trig cyclized product exclusively in good yield. The utility of pyrrolidine derivatives thus obtained from D-glucose derived γ-alkenylamines 1a and 1b was demonstrated in the synthesis of 1-deoxycastan...

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Autores principales: Dhavale, Dilip D., Jachak, Santosh M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2005
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6147711/
https://www.ncbi.nlm.nih.gov/pubmed/18007358
http://dx.doi.org/10.3390/10080893
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author Dhavale, Dilip D.
Jachak, Santosh M.
author_facet Dhavale, Dilip D.
Jachak, Santosh M.
author_sort Dhavale, Dilip D.
collection PubMed
description The intramolecular aminomercuration of γ-alkenylamines 1a, 1b and 4 was shown to afford the 5-endo-trig cyclized product exclusively in good yield. The utility of pyrrolidine derivatives thus obtained from D-glucose derived γ-alkenylamines 1a and 1b was demonstrated in the synthesis of 1-deoxycastanospermine (3a) and 1-deoxy-8a-epi-castanospermine (3b).
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spelling pubmed-61477112018-11-19 The 5-Endo-trig Cyclization of d-Glucose Derived γ-Alkenylamines with Mercury (II) Salts: Synthesis of 1-Deoxy-castanospermine and its 8a-epi-Analogue† Dhavale, Dilip D. Jachak, Santosh M. Molecules Article The intramolecular aminomercuration of γ-alkenylamines 1a, 1b and 4 was shown to afford the 5-endo-trig cyclized product exclusively in good yield. The utility of pyrrolidine derivatives thus obtained from D-glucose derived γ-alkenylamines 1a and 1b was demonstrated in the synthesis of 1-deoxycastanospermine (3a) and 1-deoxy-8a-epi-castanospermine (3b). MDPI 2005-08-31 /pmc/articles/PMC6147711/ /pubmed/18007358 http://dx.doi.org/10.3390/10080893 Text en © 2005 by MDPI (http://www.mdpi.org). Reproduction is permitted for non commercial purposes.
spellingShingle Article
Dhavale, Dilip D.
Jachak, Santosh M.
The 5-Endo-trig Cyclization of d-Glucose Derived γ-Alkenylamines with Mercury (II) Salts: Synthesis of 1-Deoxy-castanospermine and its 8a-epi-Analogue†
title The 5-Endo-trig Cyclization of d-Glucose Derived γ-Alkenylamines with Mercury (II) Salts: Synthesis of 1-Deoxy-castanospermine and its 8a-epi-Analogue†
title_full The 5-Endo-trig Cyclization of d-Glucose Derived γ-Alkenylamines with Mercury (II) Salts: Synthesis of 1-Deoxy-castanospermine and its 8a-epi-Analogue†
title_fullStr The 5-Endo-trig Cyclization of d-Glucose Derived γ-Alkenylamines with Mercury (II) Salts: Synthesis of 1-Deoxy-castanospermine and its 8a-epi-Analogue†
title_full_unstemmed The 5-Endo-trig Cyclization of d-Glucose Derived γ-Alkenylamines with Mercury (II) Salts: Synthesis of 1-Deoxy-castanospermine and its 8a-epi-Analogue†
title_short The 5-Endo-trig Cyclization of d-Glucose Derived γ-Alkenylamines with Mercury (II) Salts: Synthesis of 1-Deoxy-castanospermine and its 8a-epi-Analogue†
title_sort 5-endo-trig cyclization of d-glucose derived γ-alkenylamines with mercury (ii) salts: synthesis of 1-deoxy-castanospermine and its 8a-epi-analogue†
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6147711/
https://www.ncbi.nlm.nih.gov/pubmed/18007358
http://dx.doi.org/10.3390/10080893
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