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†

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Received: 15 October 2004; in revised form: 4 January 2005 / Accepted: 10 January 2005 / Published: 31 August 2005
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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.
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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.

AMA 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(8):893-900.

Chicago/Turabian Style

Dhavale, D.; Jachak, S. 2005. "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 10, no. 8: 893-900.

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