Stereochemistry of sagittamide A: Prediction and confirmation

Organic Letters

Volumn 8, Issue 17, 2006, Pages 3865-3868

  Seike, Hirofumi ^a   Ghosh, Indranath ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; DRUG DERIVATIVE; ORNITHINE; SAGITTAMIDE A; VALINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM;

BIOLOGICAL PRODUCTS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; ORNITHINE; STEREOISOMERISM; VALINE;

EID: 33748587304     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061582d     Document Type: Article

References (19)

1. Lievens, S. C.; Molinski, T. F. Org. Lett. 2005, 7, 2281.
2. Seike, H.; Ghosh, I.; Kishi, Y. Org. Lett. 2006, 8, 3861.
3. Higashibayashi, S.; Czechtizky, W.; Kobayashi, Y.; Kishi, Y. J. Am. Chem. Soc. 2003, 125, 14379.
4. The second best candidate was found to be the SAA (Σ|ΔHz| = 4.9 Hz) or AAS (Σ|ΔHz| = 4.9 Hz) subgroup for comparison B, the ASS subgroup (Σ|ΔHz| = 5.2 Hz) for comparison C, and the SAS subgroup (Σ|ΔHz| = 4.2 Hz) for comparison D, respectively. However, the degree of profile fitness well exceeds the level of Σ|ΔHz| < 3.3 Hz for all these cases.
5. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
6. (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
7. (a) Dormoy, J. R.; Castro, B. In Encylopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons Ltd.: Chichester, U.K., 1995; Vol. 1, pp 301-304.
8. (b) Castro, B.; Dormoy, J. R.; Evin, G.; Selve, C. Tetrahedron Lett. 1975, 1219.
9. (a) Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3943.
10. (b) Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3947.
11. (c) Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron 1984, 40, 2247.
12. Hughes, D. L. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons. Inc.: Hoboken, NJ, 1992; Vol. 42 pp 335-656.
13. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391.
14. Previous work in our laboratory has shown steric and/or stereoelectronic interactions between structural clusters separated by two or more carbons to be negligibly small. This characteristic, referred to as a self-contained box, constitutes one of the key foundations for our NMR database approach. For examples, see: (a) Boyle, C. D.; Harmange, J.-C.; Kishi, Y. J. Am. Chem. Soc. 1994, 116, 4995.
15. (b) Zheng, W.; DeMattei, J. A.; Wu, J.-P.; Duan, J. J.-W.; Cook, L. R.; Oinuma, H.; Kishi, Y. J. Am. Chem. Soc. 1996, 118, 7946.
16. (c) Kobayashi, Y.; Tan, C.-H.; Kishi, Y. Helv. Chim. Acta 2000, 83, 2562.
17. (d) Kobayashi, Y.; Tan, C.-H.; Kishi, Y. J. Am. Chem. Soc. 2001, 123, 2076. Also see ref 3 and references therein.
18. This was due to a partial epimerization of the D-valine moiety during the preparation of D-valine tert-butyl ester.
19. In addition to the three doubled acetyl signals, the resonance around 2.08 ppm showed a sign of doubling.