Synthesis of 1,4-diaminocyclitols from L-serine methyl ester

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5528-5531

  Kang, Min ^a   Park, Jeonghan ^a   Konradi, Andrei W ^a   Pedersen, Steven F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE; POLYOL;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029784980     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960691a     Document Type: Article

References (20)

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3. (c) Egan, R. S.; Stanaszek, R. S.; Cirovic, M.; Mueller, S. L.; Tadanier, J.; Martin, J. R.; Collum, P.; Goldstein, A. W.; De Vault, R. L.; Sinclair, A. C.; Fager, E. E.; Mitscher, L. A. J. Antibiot. 1977, 30, 552.
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10. (a) Freudenberger, J. H.; Konradi, A. W.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 8014.
11. (b) Takahara, P. M.; Freudenberger, J. H.; Konradi, A. W.; Pedersen, S. F. Tetrahedron Lett. 1989, 30, 7177.
12. (c) Konradi, A. W.; Pedersen, S. F. J. Org. Chem. 1990, 55, 4506.
13. (d) Park, J.; Pedersen, S. F. J. Org. Chem. 1990, 55, 5924.
14. (e) Raw, A. S.; Pedersen, S. F. J. Org. Chem. 1991, 56, 830.
15. (f) Konradi, A. W.; Pedersen, S. F. J. Org. Chem. 1992, 57, 28.
16. (g) Park, J.; Pedersen, S. F. Tetrahedron 1992, 48, 2069.
17. (h) Konradi, A. W.; Kemp, S. J.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316.
18. 1H NMR spectroscopy and gas chromatography.
19. For the intramolecular pinacol coupling reaction of 1,4-ketoaldehydes, we found that the addition of 5 equiv of DMF increases the yield of cyclized product. See ref 3e.
20. The stereochemistry of 11 was confirmed by X-ray analysis of a derivative, 13. The authors have deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK. (Equation Presented)