Computer-assisted constitutional assignment of large molecules: COCON analysis of ascomycin

Organic Letters

Volumn 1, Issue 5, 1999, Pages 737-740

  Junker, Jochen ^a   Maier, Walter ^b   Lindel, Thomas ^c   Köck, Matthias ^a  

^a GOETHE UNIVERSITY   (Germany)

^b BASF SE   (Germany)

^c Pharmazeutisch Chemisches I der U   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001658012     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990725b     Document Type: Article

References (15)

1. (a) Lindel, T.; Junker, J.; Köck, M. J. Mol. Model. 1997, 3, 364-368.
2. (b) Lindel, T.; Junker, J.; Köck, M. Eur. J. Org. Chem. 1999, 573-577.
3. (c) Köck, M.; Junker, J.; Maier, W.; Will, M.; Lindel, T. Eur. J. Org. Chem. 1999, 579-586.
4. Jaspers, M. Nat. Prod. Rep. 1999, 16, 241-248, and references cited therein.
5. Or, Y. S.; Clark, R. F.; Xie, Q.; McAlpine, J.; Whittern, D. N.; Henry, R.; Luly, J. R. Tetrahedron 1993, 49, 8771-8786.
6. Aue, W. P.; Bartholdi, E.; Ernst, R. R. J. Chem. Phys. 1976, 64, 2229-2246.
7. Bax, A.; Summers, M. F. J. Am. Chem. Soc. 1986, 108, 2093-2094.
8. 1 (factor of 2).
9. Ley, S. V.; Doherty, K.; Massiot, G.; Nuzillard, J.-M. Tetrahedron 1994, 50, 12267-12280.
10. Peng, C.; Yuan, S.; Zheng, C.; Shi, Z.; Wu, H. J. Chem. Inf. Comput. Sci. 1995, 35, 539-546.
11. This allows the user to number the atoms, for example, first by the order number and then by the decreasing carbon chemical shift. Since the HMBC correlations are given from protons to carbons, the first entries are usually nonprotonated carbons and therefore without HMBC correlations. For a known compound a given numbering might be used and therefore the resulting input file is unpredictable.
12. The presorting is also advantageous for the detection of constitutionally equivalent isomers because identical atoms with identical connectivities are automatically set in one group.
13. The correlation data used for the COCON analysis of haemoventosin were originally obtained for the O-acetyl derivative.
14. Maier, W. In Computer - Enhanced Analytical Spectroscopy; Wilkins, C. L., Ed.; Plenum Press: New York, London, 1993; Vol. 4, pp 37-55.
15. The calculation time was 15 min on a SGI R10000 (195 MHz).