Variable strategy toward carbasugars and relatives as illustrated by diastereoselective synthesis of 1-deoxy-1-amino-pseudo-β-d-gulopyranose (alias 1,2,4-tri-epi-validamine)

Organic Letters

Volumn 1, Issue 8, 1999, Pages 1213-1215

  Rassu, Gloria ^a   Auzzas, Luciana ^a   Pinna, Luigi ^a   Zanardi, Franca ^a   Battistini, Lucia ^a   Casiraghi, Giovanni ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000364971     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990880q     Document Type: Article

References (21)

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10. For general reviews on the use of furan-, pyrrole-, and thiophene-based 2-silyloxy dienes, see: (a) Casiraghi, G.; Rassu, G. Synthesis 1995, 607-629.
11. (b) Casiraghi, G.; Rassu, G.; Zanardi, F.; Battistini, L. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Stamford; 1998; Vol. 3, pp 113-189.
12. For recent syntheses of validamine and related stereoisomers, see: (a) Shing, T. K. M.; Tai, V. W.-F. J. Org. Chem. 1995, 60, 5332-5334.
13. (b) Aceña, J. L.; Arjona, O.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 6419-6424.
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19. 3) δ 176.2, 145.1, 82.6, 74.2, 72.2, 70.2, 59.4, 48.9, 28.1 (3C), 27.1, 26.3 (3C), 25.8 (3C), 18.0 (2C), 6.8 (3C), 5.1 (3C), -4.0, -4.2 (2C), -4.7.
20. Methanolysis of lactam 8 cleanly afforded the corresponding amino acid ester, a nice example of functional, conformationally restricted GABA analogue.
21. 3) δ 171.7, 170.8, 169.9, 169.1 (2C), 70.7, 68.4, 68.3, 63.2, 47.4, 33.9, 29.1, 23.4, 20.9 (2C), 20.7 (2C).