Electrophile-Initiated Cyclobutane Ring Cleavage of (+)-cis -3-Methylnopinone

Journal of Organic Chemistry

Volumn 54, Issue 7, 1989, Pages 1536-1538

  Kato, Michiharu ^a   Kamat, Vijayendra P ^a   Tooyama, Youichi ^a   Yoshikoshi, Akira ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001294825     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00268a012     Document Type: Article

References (14)

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2. Wallach, O.; Blumann, A. Justus Liebigs Ann. Chem. 1907, 356, 231.
3. Rimini, E. Gazz. Chim. Ital. 1916, 46,119. Lewis, K. G.; Williams, G. J. Aust. J. Chem. 1968, 21, 2467. Bessiere-Chretien, Y.; Brahim Maklati, M. Compt. Rend. 1969, 269. 1315.
4. Mayer, C. F.; Crandall, J. K. J. Org. Chem. 1970, 35, 2688. Coxon, J. M.; Garland, R. R.; Hartshorn, M. P. Aust. J. Chem. 1972, 25, 2407.
5. Van Der Gen, A.; Van Der Linde, L. M.; Witteveen, J. G.; Boelens, H. Recl. Trav. Chim. Pays-Bas 1971, 90, 1034.
6. (b) For a discussion of this racemization, see: Yanami, I.; Miyashita, M.; Yoshikoshi, A. J. Org. Chem. 1980, 45. 607.
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8. (Synthesis of racemic 5) Odom, H. C.; Pinder, A. R. J. Chem. Soc., Perkin Trans. I 1972. 2193.
9. Levine. S. G.: Gopalakrishnan. B. Tetrahedron Lett. 1979. 699.
10. Konopelsky, J. P.; Sundararaman, P.; Barth, G.; Djerassi, C. J. Am. Chem. Soc. 1980, 102, 2737. (b) Konopelsky, J. P.; Djerassi, C. J. Org. Chem. 1980, 45, 2297. (c) Lee, S. F.; Edgar, M.; Pak. C. S.; Barth. G.; Dierassi, C. J. Am. Chem. Soc. 1980, 102. 4784.
11. (The ring cleavage of a more complex nopinone structure with BBr3Boger, D. L.; Mullican, M. D.; Hellberg, M. R.; Patel, M. J. Org. Chem. 1985, 50, 1904.
12. Miller, R. D.; McKean, R. J. Org. Chem. 1981, 46, 2412. (b) Rigby, J. H.; Senanayake, C. J. Org. Chem. 1988,53, 440. (c) Giacomin, E.; Loreto, M. A.; Pellacani, L.; Tardella, P. A. J. Org. Chem. 1980, 45, 519. (d) Dieter, R. K.; Pounds, S. J. Org. Chem. 1982, 47, 3174. (e) Demuth. M.; Raghavan P. K. Helv. Chim. Acta 1979, 62. 2338.
13. The [α]D value of optically pure 1 has been estimated. Grimshaw, J.; Grimshaw, J. T.; Juneja, H. R. J. Chem. Soc.; Perkin Trans. 1 1972, 50.
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