Structural and synthetic studies on the retrofractamides—amide constituents of Piper retrofractum |
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Authors: | Avijit Banerji Debabrata Bandyopadhyay Manjusha Sarkar Arup K Siddhanta Sudhir C Pal Somnath Ghosh Koshy Abraham James N Shoolery |
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Institution: | 1. Pure Chemistry Department, Science College, University of Calcutta, Calcutta 700009, India;2. Regional Research Centre, Government Central Pharmacy, Jayanagar, Bangalore 560011, India;3. Varian Associates, Palo Alto, CA 94303, U.S.A. |
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Abstract: | Two new unsaturated amides, retrofractamides A and C, were isolated from the total above-ground parts of Piper retrofractum. Retrofractamide A was shown to be N-isobutyl-9(3′,4′-methylenedioxyphenyl)2E,4E,8E-nonatrienamide from spectroscopic and chemical investigations. The structure 6 for retrofractamide C was suggested from spectroscopic and chemical studies and was confirmed by a total stereoselective synthesis. The presence of sesamin and 3,4,5-trimethoxydihydrocinnamic acid as well as two higher homologues of retrofractamide A, viz. pipericide (retrofractamide B) and retrofractamide D was demonstrated. The synthesis of pipericide was also achieved. |
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Keywords: | Piperaceae alkamides retrofractamides A C and D pipericide sesamin 3 4 5-trimethoxydihydrocinnamic acid |
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