Curious reduction products from a strained polycyclic quinone

Tetrahedron Letters

Volumn 40, Issue 20, 1999, Pages 3859-3862

  Zhang, Jiajia ^a   Ho, Douglas M ^a   Pascal Jr , Robert A ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC QUINONE; QUINONE DERIVATIVE; SODIUM BOROHYDRIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONFORMATION; ENERGY; REACTION ANALYSIS; REDUCTION; SYNTHESIS; X RAY ANALYSIS;

EID: 0033553498     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00643-7     Document Type: Article

References (14)

1. (1) (a) Pascal, R. A., Jr.; McMillan, W. D.; Van Engen, D. J. Am. Chem. Soc. 1986, 108, 5652-5653.
2. (b) Pascal, R. A., Jr.; McMillan, W. D.; Van Engen, D.; Eason, R. G. ibid. 1987, 109, 4660-4665.
3. (2) Fagan, P. J.; Ward, M. D.; Caspar, J. V.; Calabrese, J. C.; Krusic, P. J. J. Am. Chem. Soc. 1988, 110, 2981-2983.
4. (3) Qiao, X.; Padula, M. A.; Ho, D. M.; Vogelaar, N. J.; Schutt, C. E.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1996, 118, 741-745.
5. (4) Qiao, X.; Ho, D. M.; Pascal, R. A., Jr. Angew. Chem., Int. Ed. Eng. 1997, 36, 1531-1532.
6. (5) Pascal, R. A., Jr.; Van Engen, D. Tetrahedron Lett. 1987, 28, 293-294.
7. (6) Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
8. 2-1 is not a even a potential minimum, but a three-dimensional transition state (see Table 1).
9. (8) Cho, H.; Harvey, R. G. J. Chem. Soc., Perkin Trans. I 1976, 836-839.
10. 2 814.2872.
11. 2) = 0.1913, and S = 1.065 for 11,475 unique reflections, 705 parameters, and 3 restraints (5 reflections were suppressed).
12. (11) Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326.
13. (12) Sheldrick, G. M. SHELXTL Version 5. Siemens Analytical X-ray Instruments, Madison, Wisconsin, USA, 1996.
14. 2) = 0.1645, and S = 1.076 for 2792 unique reflections, 336 parameters, and 0 restraints.