THE SYNTHESIS OF DEOXYGALACTOSTATIN AND 2,6-IMINO-HEPTITOL DERIVATIVES VIA STANNANE MEDIATED HYDROXYMETHYLATION OF 5-AZIDO-1,4-LACTONES

Authors
SHILVOCK JP FLEET GWJ
Citation
Jp. Shilvock et Gwj. Fleet, THE SYNTHESIS OF DEOXYGALACTOSTATIN AND 2,6-IMINO-HEPTITOL DERIVATIVES VIA STANNANE MEDIATED HYDROXYMETHYLATION OF 5-AZIDO-1,4-LACTONES, Synlett, (5), 1998, pp. 554
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
5
Year of publication
1998
Database
ISI
SICI code
0936-5214(1998):5<554:TSODA2>2.0.ZU;2-7
Abstract
Deoxygalactostatin, homogalactonojirimycin derivatives and other 2,6-i mino-heptitols are accessed via the nucleophilic addition of a hydroxy methyl anion equivalent to 5-azido-1,4-lactones to afford 6-azido-lact ols. Subsequent hydrogenation induces intramolecular reductive aminati on to produce the desired piperidine ring systems.