Asymmetric routes to azasugars from chiral bicyclic lactams. Synthesis of 1,4-dideoxy-1,4-imino-D-lyxitol; L-deoxymannojirimycin; rhammo-1-deoxynojirimycin and 1-deoxy-6-epicastanospermine

Meyers, A. I.; Andres, C. J.; Resek, James E.; Woodall, Charlotte C.; McLaughlin, Maureen A.; Lee, Peter H.; Price, David A.

doi:10.1016/s0040-4020(99)00454-8

Cited by 71 publications

(16 citation statements)

References 49 publications

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“…We were thus interested in the particular reactivity of cyclic γ‐keto‐acids. The particular reactivity of the ketoacids is exploited by Meyers’ team and other groups to synthesize pyrolidinones, pyrolidines, and other nitrogen containing heterocycles like azasugars (48,53–57).…”

Section: Bioinspiration: the Best Of Both Worldsmentioning

confidence: 99%

Natural Compounds: Leads or Ideas? Bioinspired Molecules for Drug Discovery

et al. 2008

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In this article, we compare drugs of natural origin to synthetic compounds and analyze the reasons why natural compounds occupy a place of choice in the current pharmacopoeia. The observations reported here support the design of synthetic compounds inspired from plant alkaloids and their biosynthetic pathway. Our reasoning leads to very efficient syntheses of compounds which complexity matches that of indolomonoterpenic alkaloids.

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Section: Bioinspiration: the Best Of Both Worldsmentioning

confidence: 99%

Natural Compounds: Leads or Ideas? Bioinspired Molecules for Drug Discovery

et al. 2008

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“…86 The initial task was the construction of the bicyclic lactam. Starting from 2,3-dihydropyran 114, hydroxymethyl-2,3-dihydropyran was formed using t-BuLi and paraformaldehyde.…”

Section: Noncarbohydrate Routes To 1-deoxynojirimycin (Dnj)mentioning

confidence: 99%

“…The same procedure with the tetraacetate of methyl b-D D-galactopyranoside 330 gave 325. 86 Starting from the known bicyclic lactam 332, oxidation at the allylic position using SeO 2 gave alcohol 333 as a single diastereomer. Treatment with OsO 4 afforded the triol, the syn hydroxyl group of which was protected as the acetonide 334.…”

Section: 6-dideoxyazasugars (Rhamnojirimycin and Fuconojirimycin Anmentioning

confidence: 99%

Recent advances in the chemistry of azapyranose sugars

Afarinkia

Bahar

2005

Tetrahedron: Asymmetry

230

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“…[1][2][3][4][5][6] This class of compounds has ability to inhibit the carbohydrate-processing enzymes glycosidases and glycosyl transferases. [7][8] Iminosugars have tremendous potential in the treatment of prominent diseases, such as cancer, [9][10][11] diabetes, 12-15 AIDS [16][17] and viral infections.…”

Section: Introductionmentioning

confidence: 99%