Biomimetic synthesis of nitraria alkaloids: stereoselective spirocyclization reactions

Wanner, Martin J.; Koomen, Gerrit‐Jan

doi:10.1016/s0040-4020(01)88473-8

Cited by 20 publications

(6 citation statements)

References 39 publications

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“…(-)-Pinidine (47) can also be obtained as Two new sedum alkaloids, homosedinone (49a), dihomosedinone (50a), and their C-6 epimers, (49b) and (50b), have been isolated from Sedurn acre. 30 The spectral properties of (49a) and (50a) indicated that they were homologues of the known sedinone (51). These structures were confirmed by synthesis30 from (48)31 (Scheme 13), but because of the ease of epimerization, perhaps via a reverse Michael reaction of the enol(52), it was not possible to deduce which epimers were present in S. acre.…”

Section: %mentioning

confidence: 92%

“…(-)-Pinidine (47) can also be obtained as Two new sedum alkaloids, homosedinone (49a), dihomosedinone (50a), and their C-6 epimers, (49b) and (50b), have been isolated from Sedurn acre. 30 The spectral properties of (49a) and (50a) indicated that they were homologues of the known sedinone (51). The absolute configuration ( -)-a-lobeline (65), a nicotine agonist, has been established by single crystal X-ray diffraction analysis of the hydrogen The diffraction pattern for the hydrogen bromide and hydrogen chloride show some interesting differences.…”

Section: Scheme 12mentioning

confidence: 96%

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Pyrrole, pyrrolidine, pyridine, piperidine, and azepine alkaloids

Plunkett¹

1994

Nat. Prod. Rep.

139

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Section: %mentioning

confidence: 92%

“…(-)-Pinidine (47) can also be obtained as Two new sedum alkaloids, homosedinone (49a), dihomosedinone (50a), and their C-6 epimers, (49b) and (50b), have been isolated from Sedurn acre. 30 The spectral properties of (49a) and (50a) indicated that they were homologues of the known sedinone (51). The absolute configuration ( -)-a-lobeline (65), a nicotine agonist, has been established by single crystal X-ray diffraction analysis of the hydrogen The diffraction pattern for the hydrogen bromide and hydrogen chloride show some interesting differences.…”

Section: Scheme 12mentioning

confidence: 96%

Pyrrole, pyrrolidine, pyridine, piperidine, and azepine alkaloids

Plunkett¹

1994

Nat. Prod. Rep.

139

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“…32 Between the publication of these two syntheses, Koomen et al also published a biomimetic synthesis of (AE)-nitramine (Scheme 8). 33 They chose compound 12 as a synthetic stable equivalent of key intermediate 3. This glutarimide-type alternative to 3 has been exploited throughout the years by this group to access numerous Nitraria alkaloids (vide infra).…”

Section: Edmond Gravelmentioning

confidence: 99%

Biosynthesis and biomimetic synthesis of alkaloids isolated from plants of the Nitraria and Myrioneuron genera: an unusual lysine-based metabolism

2010

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This review describes a wide panel of alkaloids isolated from plants of the Nitraria genus, focusing on their biosynthesis and discussing the resulting biomimetic chemistry in relevant cases. The scope is purposely limited to alkaloids derived at least to some extent from L-lysine, considering that most of these molecules have unique structures and are specific to the genus. Some of the biosynthetic pathways described are taken from the literature, but others are proposed here for the first time. The latter are mostly hypotheses justified by the fact that they are based on metabolic routes frequently encountered for other Nitraria alkaloids, and thus permit unification of the biosynthesis around common pivotal biosynthetic intermediates. Myrioneuron alkaloids are also presented as a newly discovered class with striking similarities to Nitraria alkaloids.

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“…Our interest in the synthesis of lupine and Nitraria alkaloids based on biosynthetic pathways (Wanner and Koomen [4] and [5]) and the fact that diamine oxidases play an important role in these biosynthetic pathways ( [6] and [7]) led us to examine the interaction of diamine oxidase with the recently isolated alkaloid nazlinin (1-(4-butylamino)Zl,2,3,4-tetrahydro-fl-carboline) (1) and its derivatives 1-(4-butylamino)-3,4-dihydro-/3-carboline (2) and l-(4-butylamino)-/3-carboline (3). (see Fig.…”

Section: R -Cho + H202 + Nhmentioning

confidence: 99%

Inhibition of pig kidney diamine oxidase by nazlinin and nazlinin derivatives

Cheng

Dekker

Gelder

et al. 1995

Biochimica et Biophysica Acta (BBA) - Protein Structure and Mol

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Nazlinin (1-(4-butylamino)-l,2,3,4-tetrahydro-/3-carboline) (1), an alkaloid recently isolated from Nitraria schoberi, and its two derivatives, 1-(4-butylamino)-3,4-dihydro-fl-carboline (2) and 1-(4-butylamino)-fl-carboline (3), were synthesized and their interaction with pig kidney diamine oxidase (PKDO) was studied. Nazlinin appeared to be a very poor substrate while 3 was a good substrate with an apparent K m of 9.3" 10 -5 M. The enzyme was inhibited by 1 and 2. With both compounds the mode of inhibition found was non-competitive and inhibition constants calculated from the slopes and intercepts of double-reciprocal plots show that 2 is a much more potent inhibitor than the natural product. The relationship between the structure of these compounds and the results found is discussed.

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Biomimetic synthesis of nitraria alkaloids: stereoselective spirocyclization reactions

Cited by 20 publications

References 39 publications

Pyrrole, pyrrolidine, pyridine, piperidine, and azepine alkaloids

Pyrrole, pyrrolidine, pyridine, piperidine, and azepine alkaloids

Biosynthesis and biomimetic synthesis of alkaloids isolated from plants of the Nitraria and Myrioneuron genera: an unusual lysine-based metabolism

Inhibition of pig kidney diamine oxidase by nazlinin and nazlinin derivatives

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