Realization of Complete Regiochemical Control during the Conversion of Squarate Esters into Complex Linear and Angular Polyquinanes. the Consequences of Incorporating a Leaving Group into One of the Alkenyllithium Reactants

Journal of Organic Chemistry

Volumn 62, Issue 6, 1997, Pages 1723-1729

  Paquette, Leo A ^a   Doyon, Julien ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030934098     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962181m     Document Type: Article

References (23)

1. Negri, J. T.; Morwick, T.; Doyon, J.; Wilson, P. D.; Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1993, 115, 12189.
2. Paquette, L. A.; Morwick, T. M. J. Am. Chem. Soc. 1995, 117, 1451.
3. Wilson, P. D.; Friedrich, D.; Paquette, L. A. J. Chem. Soc., Chem. Commun. 1995, 1351.
4. Paquette, L. A.; Morwick, T. M. J. Am. Chem.Soc. 1997, 119, 1230.
5. Morwick, T. M.; Doyon, J.; Paquette, L. A. Tetrahedron Lett. 1995, 36, 2369.
6. Rawal, V. H.; Dufour, C. J. Am. Chem. Soc. 1994, 116, 2613.
7. Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer-Verlag: New York, 1987.
8. Preliminary report: Paquette, L. A.; Doyon, J. J. Am. Chem. Soc. 1995, 117, 6799.
9. (a) Paquette, L. A.; Shi, Y.-J. J. Org. Chem. 1989, 54, 5205.
10. (b) Paquette, L. A.; Reagan, J.; Schreiber, S. L.; Teleha, C. A. J. Am. Chem. Soc. 1989, 111, 2331.
11. (c) Paquette, L. A.; Shi, Y.-J. J. Am. Chem. Soc. 1990, 112, 8478.
12. (a) Johnson, C. R.; Sakaguchi, H. Synlett 1992, 813.
13. (b) Johnson, C. R.; Adams, P. A.; Braun, M. P.; Senanayake, C. B. W.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett. 1992, 33, 917.
14. Huisgen, R.; Dahmen, A.; Huber, H. J. Am. Chem. Soc. 1967, 89, 7130.
15. (a) Shih, C.; Fritzen, E. L.; Swenton, J. S. J. Org. Chem. 1980, 45, 4462.
16. (b) Smith, A. B., III; Branca, S. J.; Piller, N. N.; Guaciaro, M. A. J. Org. Chem. 1982, 47, 1855.
17. (c) Smith, A. B., III; Branca, S. J.; Guaciaro, M. A.; Wovkulich, P. M.; Korn, A. Organic Syntheses; Wiley: New York, 1990; Collect. Vol. VII, p 271.
18. Okano, Y.; Sawa, H.; Aonuma, S.; Kato, R. Chem. Lett. 1993, 1851.
19. Ficini, J.; Kahn, P.; Falou, S.; Touzin, A. M. Tetrahedron Lett. 1979, 67.
20. (a) Roff, J. E.; Braun, R. K. Can. J. Chem. 1973, 51, 3354.
21. (b) Braun, R. K. Can. J. Chem. 1968, 46, 2283.
22. Morwick, T. M.; Paquette, L. A. J. Org. Chem, 1996, 61, 146.
23. The authors have deposited the atomic coordinates for the three X-ray structures 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, U.K.