Diastereoselective synthesis of piperidine imino sugars using Aldol additions of metalated bislactim ethers to threose and erythrose acetonides

Journal of Organic Chemistry

Volumn 73, Issue 6, 2008, Pages 2240-2255

  Ruiz, María ^a   Ruanova, Tania M ^a   Blanco, Olga ^a   Núñez, Fátima ^a   Pato, Cristina ^a   Ojea, Vicente ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL ADDITIONS; DIASTEREOSELECTIVE SYNTHESIS; ERYTHROSE ACETONIDES; METALATED BISLACTIM ETHERS;

AMINATION; AMINO ACIDS; CHIRALITY; DENSITY FUNCTIONAL THEORY; ETHERS; SYNTHESIS (CHEMICAL);

SUGARS;

1 DEOXY DEXTRO ALLONOJIRIMYCIN; 1 DEOXY DEXTRO GALACTONOJIRIMYCIN; 1 DEOXY DEXTRO GLUNOJIRIMYCIN; 1 DEOXY DEXTRO TALONOJIRIMYCIN; 1 DEOXY LEVO ALTRONOJIRIMYCIN; 1 DEOXY LEVO IDONOJIRIMYCIN; ALDEHYDE; CARBOHYDRATE DERIVATIVE; CARBON; ETHER DERIVATIVE; GLYCERALDEHYDE; GLYCINE; GLYCOSIDASE INHIBITOR; IMINE; LITHIUM CHLORIDE; PIPERIDINE DERIVATIVE; SUGAR; UNCLASSIFIED DRUG;

ADDITION REACTION; ALDOL REACTION; ALKYLATION; AMINATION; ARTICLE; ASYMMETRIC SYNTHESIS; CALCULATION; CARBOHYDRATE SYNTHESIS; CHIRALITY; CONFORMATION; DENSITY FUNCTIONAL THEORY; DIASTEREOISOMER; PROTON TRANSPORT; REDUCTION; SOLVATION; STEREOCHEMISTRY; TRANS ISOMER;

1-DEOXYNOJIRIMYCIN; ALDEHYDES; ENZYME INHIBITORS; ETHERS; GLYCINE; GLYCOSIDE HYDROLASES; IMINO SUGARS; LACTAMS; LITHIUM CHLORIDE; MODELS, MOLECULAR; PIPERIDINES; STEREOISOMERISM; TETROSES; THERMODYNAMICS; TIN;

EID: 41849092679     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702601z     Document Type: Article

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158. Other trihydroxypipecolic acids have shown important biological activities: (a) Le Merrer, Y.; Poitout, L.; Depezay, J.-C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M.-J. Bioorg. Med. Chem. 1997, 5, 519-533.
159. (b) Tsuruoka, T.; Fukuyasu, H.; Ishii, M.; Usui, T.; Shibahara, S.; Inouye, S. J. Antibiot. 1996, 49, 155-61.
160. (c) Fleet, G. W. J.; Karpas, A.; Dwek, R. A.; Fellows, L. E.; Tyms, A. S.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Smith, P. W.; Son, J. C.; Wilson, F.; Witty, D. R.; Jacob, G. S.; Rademacher, T. W. FEBS Lett. 1988, 237, 128-32.
161. Corey, E. J.; Palani, A. Tetrahedron Lett. 1995, 36, 3485-3488.
162. 2, from 0°C to rt) were unsuccessful. (a) Kim, K. S.; Cho, I. H.; Yoo, B. K.; Song, Y. H.; Hahn, C. S. J. Chem. Soc., Chem. Commun. 1984, 762-763.
163. (b) Siedlecka, R.; Skarzewski, J.; Mlochowski, J. Tetrahedron Lett. 1990, 31, 2177-2180.
164. IBX was prepared as described in: Frigerio, M.; Santagostino, M.; Sputore, S.; Palmisano, G. J. Org. Chem. 1995, 60, 7272-7276.
165. CAUTION: IBX has been reported to detonate upon heavy impact and heating over 200°C: (a) Plumb, J. B.; Harper D. J. Chem. Eng. News 1990, July 16, 3.
166. See also: (b) Dess, B. D.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.