Use of metalated enecarbamates in the squarate cascade. Direct access to highly functionalized 2,4-cyclooctadienones by intramolecular interception of the mesocyclic dienolates

Tetrahedron Letters

Volumn 38, Issue 18, 1997, Pages 3151-3154

  Paquette, Leo A ^a   Tae, Jingsung ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANE DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030976049     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00565-0     Document Type: Article

References (18)

1. Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757.
2. In 1960, Nelson Leonard suggested that "mesocycle" would be a suitable alternative defining name for medium-sized rings: footnote 4 in Leonard, N. J.; Milligan, T. W.; Brown, T. L. J. Am. Chem. Soc. 1960, 82, 4075.
3. Paquette, L A.; Kuo, L. H.; Doyon, J. J. Am. Chem. Soc. 1997, 119, 1230.
4. Paquette, L. A.; Morwick, T. J. Am. Chem. Soc. 1997, 119, in press, and relevant references cited therein.
5. (a) Paquette, L. A.; Morwick, T. J. Am. Chem. Soc. 1995, 117, 1451.
6. (b) Paquette, L. A.; Doyon, J. J. Am. Chem. Soc. 1995, 117, 6799.
7. (c) Paquette, L. A.; Morwick, T. M.; Negri, J. T.; Rogers, R. D. Tetrahedron 1996, 52, 3075.
8. (d) Paquette, L. A.; Kuo, L. H.; Doyon, J. Tetrahedron 1996, 52, 11625.
9. (a) Dieter, R. K.; Sharma, R. R. J. Org. Chem. 1996, 61, 4180.
10. (b) Meth-Cohn, O.; Westwod, K. T. J. Chem. Soc., Perkin Trans. 1 1984, 1173.
11. (c) Shono, T.; Matsumura, Y.; Tsubata, K.; Sugihara, Y.; Yamane, S.; Kanazawa, T.; Aoki, T. J. Am. Chem. Soc. 1982, 104, 6697.
12. (d) Kraus, G. A.; Neuenschwander, K. J. Org. Chem. 1981, 46, 4791.
13. Lithiation has previously been accomplished with s-butyllithium/TMEDA [Beak, P.; Lee, W. K. J. Org. Chem. 1993, 58, 1109] or via a two-step sequence proceeding through a vinylstannane [Lander, P. A.; Hegedus, L. S. J. Am. Chem. Soc. 1994, 116, 8126].
14. Lithiation has previously been accomplished with s-butyllithium/TMEDA [Beak, P.; Lee, W. K. J. Org. Chem. 1993, 58, 1109] or via a two-step sequence proceeding through a vinylstannane [Lander, P. A.; Hegedus, L. S. J. Am. Chem. Soc. 1994, 116, 8126].
15. Other structural variants on this theme have been reported: (a) Sengupta, S.; Snieckus, V. J. Org. Chem. 1990, 55, 5680.
16. (b) Weisenburger, G. A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 12218.
17. For another example of a thermodynamic preference for the cis/trans fusion of two five-membered rings to a cyclooctane core, consult Paquette, L. A.; Sun, L.-Q.; Friedrich, D.; Savage, P. B. Tetrahedron Lett. 1997, 38, 195.
18. Paquette, L. A.; Broadhurst, M. J. J. Org. Chem. 1973, 38, 1886.