ISSN:
0170-2041
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Synthesis, Spectroscopic Examination, and Testing for Antibacterial Activity of Some Pepper Alkaloids. Olefination Reactions with Phosphorylacetamides4,5-Dihydrowisanine (4) and 4,5-dihydrookolasine (3) as well as 1-(2-methoxy-4,5-methylene-dioxycinnamoyl)piperidine (5) are three alkaloids which have been isolated from Piper guineense and Piper peepuloides, respectively. They have been synthesized by Horner-Wittig reaction of 3-(2-methoxy-4,5-methylenedioxyphenyl)propionaldehyde (11) and 2-methoxy-4,5-methylene-dioxybenzaldehyde (8) with 1-(diethoxyphosphorylacetyl)piperidine (6) and -pyrrolidine (7), respectively. The Horner-Wittig reaction gave products having E-configuration. The amides are not or only slightly active against bacteria.
Notes:
4,5-Dihydrowisanin (4) und 4,5-Dihydrookolasin (3) sowie 2-Methoxy-4,5-methylendioxyzimtsäure-piperidid (5) sind drei aus Piper guineense bzw. Piper peepuloides isolierte Alkaloide. Sie wurden durch Horner-Wittig-Reaktion von 3-(2-Methoxy-4,5-methylendioxyphenyl)propionaldehyd (11) bzw. 2-Methoxy-4,5-methylendioxybenzaldehyd (8) mit 1-(Diethoxyphosphoryl-acetyl)piperidin (7) bzw. -pyrrolidin (6) hergestellt. Die Horner-Wittig-Reaktion ergab Verbindungen mit E-Konfiguration. Die Amide sind nicht oder nur schwach antibakteriell wirksam.
Additional Material:
5 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198219820615
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