Computationally guided organometallic chemistry: Preparation of the heptacyclic pyrazine core of ritterazine N

Journal of Organic Chemistry

Volumn 71, Issue 7, 2006, Pages 2797-2801

  Taber, Douglass F ^a   Taluskie, Karen V ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOZIRCONATION; HEPTACYCLIC PYRAZINE; PYRAZINE; WITTIG HOMOLOGATION;

ALDEHYDES; COMPUTATIONAL METHODS; ESTERS; KETONES; NITROGEN COMPOUNDS;

ORGANOMETALLICS;

ALKADIENE; ALPHA AZIDO KETONE; CEPHALOSTATIN; NATURAL PRODUCT; PYRAZINE DERIVATIVE; RITERRAZINE N; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CYCLOADDITION; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; MATHEMATICAL ANALYSIS; ORGANIC CHEMISTRY; STRUCTURE ANALYSIS;

COMPUTER SIMULATION; CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; PYRAZINES; SPIRO COMPOUNDS; STEREOISOMERISM; STEROIDS; ZIRCONIUM;

EID: 33645524524     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052656m     Document Type: Article

References (22)

1. For the isolation and activity of the ritterazines and cephalostatins, see: (a) Pettit, G. R.; Tan, R.; Xu, J.; Ichihara, Y.; Williams, M. D.; Boyd, M. R. J. Nat. Prod. 1998, 61, 955.
2. (b) Fukuzawa, S.; Matsunaga, S.; Fusetani, N. J. Org. Chem. 1997, 62, 4484.
3. Ganesan, A. Angew. Chem., Int. Ed. Engl 1996, 35, 611.
4. For the physiological activity of the cephalostatins and ritterazines, see: (a) Komiya, T.; Fusetani, N.; Matsunaga, S.; Kubo, A.; Kaye, F. J.; Kelley, M. J.; Tamura, K.; Yoshida, M.; Fukuoka, M.; Nakagawa, K. Cancer Chemother. Pharm. 2003, 51, 202.
5. (b) Dirsch, V. M.; Mueller, I. M.; Eichhorst, S. T.; Pettit, G. R.; Kamano, Y.; Inoue, M.; Xu, J. P.; Ichihara, Y.; Wanner, G.; Vollmar, A. M. Cancer Res. 2003, 63, 8869.
6. (c) Mueller, I. M.; Dirsch, V. M.; Rudy, A.; Lopez-Anton, N.; Pettit, G. R.; Vollmar, A. M. Mol. Pharm. 2005, 67, 1684.
7. For leading references to the synthesis of the fused 6-5 cephalostatins and ritterazines, see: (a) Li, W.; Fuchs, P. L. Org. Lett. 2003, 5, 2849.
8. (b) Flessner, T.; Jautelat, R.; Scholz, U.; Winterfeldt, E. Prog. Chem. Org. Nat. Prod. 2004, 87, 1.
9. (c) Tietze, L. F.; Krahnert, W. R.; Chem. Eur. J. 2002, 8, 2116.
10. No work has yet been reported toward the spiro 5-5 ritterazines. (5) For the development of intramolecular diene cyclozirconation, including computational analysis, see: (a) Nugent, W. A.; Taber, D. F. J. Am. Chem. Soc. 1989, 111, 6435.
11. (b) Taber, D. F.; Louey, J. P.; Wang, Y.; Nugent, W. A.; Dixon, D. A.; Harlow, R. L. J. Am. Chem. Soc. 1994, 116, 9457.
12. For the development of Zr-based intramolecular diene cyclocarbonylation, including computational analysis, see: (a) Negishi, E.; Miller, S. R. J. Org. Chem. 1989, 54, 6014.
13. (b) Taber, D. F.; Wang, Y. J. Am. Chem. Soc. 1997, 119, 22.
14. (c) Taber, D. F.; Zhang, W.; Campbell, C. L.; Rheingold, A. R.; Incarvito, C. D. J. Am. Chem. Soc. 2000, 122, 4813.
15. (d) Both ZINDO and molecular mechanics were used as implemented on a Tektronix CAChe workstation.
16. (a) Cahiez, C.; Alexakis, A.; Normant, J. F. Synthesis 1978, 528.
17. (b) Johnston, B. D.; Oehlschlager, A. C. Can. J. Chem. 1984, 62, 2148.
18. Forcellese, M. L.; Calvitti, S.; Camerini, E.; Martucci, I.; Mincione, E. J. Org. Chem. 1985, 50, 2191.
19. Campbell, M. M.; Craig, R. C.; Boyd, A. C.; Gilbert, I. M.; Logan, R. T.; Redpath, J.; Roy, R. G.; Savage, D. S.; Sleigh, T. J. Chem. Soc., Perkin Trans. 1 1979, 2235.
20. Heathcock, C. H.; Smith, S. C. J. Org. Chem. 1994, 59, 6828.
21. (a) Suzuki, H.; Kawaguchi, T.; Takaoka, K. Bull Chem. Soc. Jpn. 1986, 59, 665.
22. (b) Jeong, J. U.; Sutton, S. C.; Kim, S.; Fuchs, P. L. J. Am. Chem. Soc. 1995, 117, 10157.