Next Article in Journal
Synthesis of Cyclophellitol Utilizing a Palladium Chloride Mediated-Ferrier-II Rearrangement
Previous Article in Journal
Bi(OTf)3 and SiO2-Bi(OTf)3 as Effective Catalysts for the Ferrier Rearrangement#
Article Menu

Export Article

Open AccessArticle
Molecules 2005, 10(8), 893-900; https://doi.org/10.3390/10080893

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

Department of Chemistry, Garware Research Centre, University of Pune, India
*
Author to whom correspondence should be addressed.
Received: 15 October 2004 / Revised: 4 January 2005 / Accepted: 10 January 2005 / Published: 31 August 2005
Full-Text   |   PDF [126 KB, uploaded 18 June 2014]   |  

Abstract

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). View Full-Text
Keywords: Aminosugars; aminomercuration; alkaloids; enzyme inhibitors; nitrones. Aminosugars; aminomercuration; alkaloids; enzyme inhibitors; nitrones.
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
SciFeed

Share & Cite This Article

MDPI and ACS Style

Dhavale, D.; Jachak, S. The 5-Endo-trig Cyclization of D-Glucose Derived γ-Alkenylamines with Mercury (II) Salts: Synthesis of 1-Deoxycastanospermine and its 8a-epi-Analogue†. Molecules 2005, 10, 893-900.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top