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Your search keyword '"Swainsonine analogs & derivatives"' showing total 5 results
Start Over Descriptor "Swainsonine analogs & derivatives" Journal organic letters
5 results on '"Swainsonine analogs & derivatives"'

1. Pd(II)-Catalyzed Aminofluorination of Alkenes in Total Synthesis 6-(R)-Fluoroswainsonine and 5-(R)-Fluorofebrifugine.

Author

Wu L, Chen P, and Liu G

Subjects
Alkaloids chemistry, Catalysis, Molecular Structure, Piperidines chemistry, Pyridines chemistry, Quinazolines chemistry, Stereoisomerism, Swainsonine chemical synthesis, Swainsonine chemistry, Alkaloids chemical synthesis, Alkenes chemistry, Palladium chemistry, Piperidines chemical synthesis, Quinazolines chemical synthesis, Swainsonine analogs & derivatives
Abstract

The total syntheses of two fluorinated alkaloids, 6-(R)-fluoroswainsonine and 5-(R)-fluorofebrifugine, are described. Both encompass (4aS,7R,8aR)-7-fluoro-5-tosylhexahydro-4H-[1,3]dioxino[5,4-b]pyridine as a key synthon which is obtained through a further optimized palladium-catalyzed aminofluorination of alkenes with high diastereoselectivity. 6-(R)-Fluoroswainsonine is synthesized from the key synthon in 14 steps, and 5-(R)-fluorofebrifugine requires a sequential 15-step transformation.

Published
2016
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2. Synthesis from D-altrose of (5R,6R,7R,8S)-5,7-dihydroxy-8-hydroxymethylconidine and 2,4-dideoxy-2,4-imino-D-glucitol, azetidine analogues of swainsonine and 1,4-dideoxy-1,4-imino-D-mannitol.

Author

Araújo N, Jenkinson SF, Martínez RF, Glawar AF, Wormald MR, Butters TD, Nakagawa S, Adachi I, Kato A, Yoshihara A, Akimitsu K, Izumori K, and Fleet GW

Subjects
Azetidines chemistry, Cyclization, Imino Furanoses chemical synthesis, Imino Furanoses chemistry, Mannitol chemical synthesis, Mannitol chemistry, Mannosidases antagonists & inhibitors, Molecular Structure, Polymers chemistry, Sorbitol analogs & derivatives, Structure-Activity Relationship, Swainsonine chemistry, Azetidines chemical synthesis, Hexoses chemistry, Mannitol analogs & derivatives, Polymers chemical synthesis, Swainsonine analogs & derivatives, Swainsonine chemical synthesis
Abstract

Ring closure of a 3,5-di-O-triflate derived from D-altrose with benzylamine allowed the formation of both monocyclic and bicyclic azetidine analogues of swainsonine.

Published
2012
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3. Synthesis of (-)-swainsonine and (-)-8-epi-swainsonine by the addition of allenylmetals to chiral α,β-alkoxy sulfinylimines.

Author

Louvel J, Chemla F, Demont E, Ferreira F, and Pérez-Luna A

Subjects
Alcohols chemistry, Imines chemistry, Molecular Structure, Stereoisomerism, Sulfinic Acids chemistry, Swainsonine chemistry, Swainsonine analogs & derivatives, Swainsonine chemical synthesis
Abstract

The asymmetric synthesis of (-)-swainsonine and (-)-8-epi-swainsonine is reported through the addition of either the allenylzinc or the allenyl lithio cyanocuprate reagents derived from [3-(methoxymethoxy)prop-1-ynyl]trimethylsilane to enantiopure α,β-dialkoxy N-tert-butanesulfinylimines derived from d-erythronolactone.

Published
2011
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4. Divergent cycloaddition and ring-closing metathesis approaches to indolizidine and pyrrolo[1,2-a]azepine skeletons from a chiral precursor: an expeditious route to (-)-8-epi-swainsonine triacetate.

Author

Nath M, Mukhopadhyay R, and Bhattacharjya A

Subjects
Alkaloids chemical synthesis, Alkaloids chemistry, Cyclization, Indolizines chemical synthesis, Indolizines chemistry, Molecular Structure, Pyrroles chemical synthesis, Pyrroles chemistry, Swainsonine chemistry, Swainsonine analogs & derivatives, Swainsonine chemical synthesis
Abstract

[reaction: see text] A divergent strategy for the synthesis of diverse azabicyclic ring systems has been developed in which a chiral N-allylpyrrolidine derivative, obtained from a carbohydrate precursor was converted to (-)-8-epi-swainsonine triacetate by RCM and to a pyrrolo[1,2-a]azepine derivative and a 3-hydroxymethyl-substituted indolizidine by N-allylcarbohydrate nitrone and nitrile oxide cycloadditions.

Published
2006
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5. Synthesis of the new mannosidase inhibitors, diversity-oriented 5-substituted swainsonine analogues, via stereoselective Mannich reaction.

Author

Fujita T, Nagasawa H, Uto Y, Hashimoto T, Asakawa Y, and Hori H

Subjects
Models, Molecular, Molecular Structure, Stereoisomerism, Swainsonine chemical synthesis, Enzyme Inhibitors chemical synthesis, Mannosidases antagonists & inhibitors, Swainsonine analogs & derivatives
Abstract

5alpha-substituted swainsonine analogues were synthesized by Mannich reaction of an in situ generated (-)-swainsonine iminium ion intermediate. 5alpha-substituted swainsonine analogues were epimerized to their 5beta-isomers in protic solvent. [reaction: see text]

Published
2004
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