2008
DOI: 10.2174/138527208786241484
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Stereoselective Syntheses of 2,6-disubstituted Piperidin-3-oles (alkaloid lipids)

Abstract: Alkaloid lipids comprise a class of natural compounds with significant biological activities of medicinal interest. Their structural framework consists of a 2,6-disubstituted-3-piperidinol moiety (polar head group) and a lipid tail. Representative examples of alkaloid lipids are (+)-Cassine, ( )-Prosophylline, ( )-Prosopinine, ( )-Spectalline.Many synthetic strategies have been developed for the efficient stereoselective synthesis of various natural alkaloid lipids and their synthetic analogues. This mini-revi… Show more

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Cited by 21 publications
(5 citation statements)
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“…Among small- and medium-size aza-heterocycles, azetidines have attracted less attention than aziridines, pyrrolidines, and piperidines, mainly due to the lack of general methods for their preparation. Recently, four-membered nitrogen-containing heterocycles have found applicability in pharmacy as highly biologically active compounds .…”
Section: Introductionmentioning
confidence: 99%
“…Among small- and medium-size aza-heterocycles, azetidines have attracted less attention than aziridines, pyrrolidines, and piperidines, mainly due to the lack of general methods for their preparation. Recently, four-membered nitrogen-containing heterocycles have found applicability in pharmacy as highly biologically active compounds .…”
Section: Introductionmentioning
confidence: 99%
“…1a-d Several recent reviews have been published covering pharmaceutically active compounds, 2 spiro-derivatives, 3a-b marine alkaloids, 4 iminosugar di-and oligosaccharides, 5a-b and alkaloid lipids. 6 Advances in synthetic methods include catalytic asymmetric aza Diels-Alder reactions, 7 benzotriazole mediated syntheses, 8 asymmetric synthesis, 9a-b and cyclization of allylsilyl-substituted N-acyliminium and iminium ions. 10 A special case of the preparation of n-membered non-aromatic azacycles is a ring expansion of (n-1) cyclic precursors fused to aziridine ring.…”
Section: Introductionmentioning
confidence: 99%
“…The cis-relationship between the 2-substituent and the 5-hydroxyl group is seen in natural products such as 5-hydroxysedamine, azimic acid, carpamic acid, cassine, and others …”
mentioning
confidence: 99%