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Journal ArticleDOI

Synthesis of retrofractamide A

01 Jan 1987-Phytochemistry (Pergamon)-Vol. 26, Iss: 12, pp 3345-3346
About: This article is published in Phytochemistry.The article was published on 1987-01-01. It has received 3 citation(s) till now. The article focuses on the topic(s): Piper retrofractum & Piperaceae.

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Topics: Piper retrofractum (72%), Piperaceae (58%)
Citations
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Journal ArticleDOI
01 Nov 1995-Phytochemistry
Abstract: Extraction of the stems and leaves of Piper ridleyi with ether afforded N - iso butyl-15-(3′,4′-methylenedioxyphenyl)-2 E ,4 E ,12 E -pentadecatrienamide (ridleyamide), as well as the known amide, retrofractamide, and sterols.

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18 citations


Journal ArticleDOI
Yu Luo1, Haomin Liu1, Mingbo Su, Li Sheng  +3 moreInstitutions (1)
TL;DR: Two natural piperamides and their derivatives were synthesized and evaluated for inhibitory activity against histone deacetylases, as well as the HCT-116 human colon cancer cell line.

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Abstract: Two natural piperamides (piperlonguminine and refrofractamide A) and their derivatives were synthesized and evaluated for inhibitory activity against histone deacetylases, as well as the HCT-116 human colon cancer cell line. The preliminary structure activity relationship was discussed. Compounds featuring a hydroxamic acid moiety exhibited moderate HDAC activity and in vitro cytotoxicity.

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9 citations


Journal ArticleDOI
TL;DR: A total synthesis of guineensine, a secondary metabolite of the Piperaceae family, has been executed in 12 steps with an overall yield of 27% and featured novel application of a Julia–Kocienski olefination reaction which effectively constructed alkenamide skeleton.

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Abstract: A total synthesis of guineensine, a secondary metabolite of the Piperaceae family, has been executed in 12 steps with an overall yield of 27%. Key steps in the synthesis featured novel application of a Julia-Kocienski olefination reaction which effectively constructed alkenamide skeleton. This contributes a unique approach to the synthesis of the piperamide alkaloids.

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7 citations


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Journal ArticleDOI
05 Feb 1985-Phytochemistry
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)2 E ,4 E ,8 E -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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41 citations


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20112
19951