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Molecules 2005, 10(8), 893-900; doi:10.3390/10080893
Article

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

*  and
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
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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).
Keywords: Aminosugars; aminomercuration; alkaloids; enzyme inhibitors; nitrones. Aminosugars; aminomercuration; alkaloids; enzyme inhibitors; nitrones.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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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.

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