Study of the intramolecular cyclization of N-methyl-3-phenyl- N-(2-( E)-phenylethenyl)- trans( cis)-oxiranecarboxamide – Syntheses of Homoclausenamide and Dehydroclausenamide

Homoclausenamide was synthesized for the first time, and the intramolecular cyclization study of N-methyl-3-phenyl- N-(2-( E)-phenylethenyl)- trans( cis)-oxiranecarboxamide well demonstrated how the stereochemistry affects the cyclization paths. Under Lewis acid condition, compound 8 undergoes cycli...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2008-08, Vol.43 (8), p.1781-1784
Main Authors: Ma, Nianchun, Wu, Kemei, Huang, Liang
Format: Article
Language:English
Subjects:
Amides
Amides - chemistry
Bicyclic compound
Biomimetic syntheses
Chemistry
Cyclization
Dehydroclausenamide
Ethylene Oxide - chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Homoclausenamide
Hydrogen - chemistry
Lactams - chemical synthesis
Lactams - chemistry
Lignans - chemical synthesis
Lignans - chemistry
Methylation
Molecular Structure
Organic chemistry
Preparations and properties
Structure-Activity Relationship
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Summary:Homoclausenamide was synthesized for the first time, and the intramolecular cyclization study of N-methyl-3-phenyl- N-(2-( E)-phenylethenyl)- trans( cis)-oxiranecarboxamide well demonstrated how the stereochemistry affects the cyclization paths. Under Lewis acid condition, compound 8 undergoes cyclizations to give Homoclausenamide and Dehydroclausenamide. [Display omitted]
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2007.11.022