Diastereofacialselectivity in Intramolecular Pauson-Khand Cycloaddition: Highly Stereoselective Synthesis of Pentalenene

Journal of the American Chemical Society

Volumn 110, Issue 15, 1988, Pages 5224-5225

  Schore, Neil E ^a   Rowley, Elizabeth G ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PENTALENENE; UNCLASSIFIED DRUG;

DRUG SYNTHESIS; METHODOLOGY; NONHUMAN; PRELIMINARY COMMUNICATION;

EID: 0023765538     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00223a069     Document Type: Article

References (11)

1. Knudsen, M. J.; Schore, N. E. J. Org. Chem. 1984, 49, 5025. (b) Schore, N. E.; Knudsen, M. J. J. Org. Chem. 1987, 52, 569.
2. Isolation: Seto, H.; Yonehara, H. J. Antibiot. 1980, 33, 92.
3. Syntheses: (a) Paquette, L. A.; Annis, G. D. J. Am. Chem. Soc. 1982, 104, 4504; 1983, 105, 7358. (b) Ohfune, Y.; Shirahama, H.; Matsumoto, T. Tetrahedron Lett. 1976, 2869. (c) Misumi, S.; Matsushima, H.; Shirahama, H.; Matsumoto, T. Chem. Lett. 1982, 855. (d) Piers, E.; Karunaratne, V. J. Chem. Soc., Chem. Commun. 1984, 959. (e) Pattenden, G.; Teague, S. J. Tetrahedron Lett. 1984, 3021. (f) Mehta, G.; Rao, K. S. J. Chem. Soc., Chem. Commun. 1985, 1464. (g) Crimmins, M. T.; DeLoach, J. A. J. Am. Chem. Soc. 1986, 108, 800. (h) Hua, D. H. J. Am. Chem. Soc. 1986, 108, 3835. (i) Mehta, G.; Rao, K. S. J. Am. Chem. Soc. 1986, 108, 8015. (j) Imanishi, T.; Ninbari, F.; Yamashita, M.; Iwata, C. Chem. Pharm. Bull. 1986, 34, 2268. (k) Hudlicky, T.; Natchus, M. G.; Sinai-Zingde, G. J. Org. Chem. 1987, 52, 4644. (1) Pattenden, G.; Teague, S. J. Tetrahedron 1987, 43, 5637.
4. Stenke, J. E.; Chamberlin, A. R.; Bond, F. T. J. Org. Chem. 1978, 43, 147. (b) Chamberlin, A. R.; Bond, F. T. J. Org. Chem. 1978, 43, 154.
5. Yamamoto, Y.; Maruyama, K. J. Am. Chem. Soc. 1978, 100, 3240. (b) Yamamoto, Y.; Yamamoto. S.; Yatagai, H.; Ishihara, Y.; Maruyama, K. J. Org. Chem. 1982, 47, 119.
6. Kende, A.; Jungheim, L. N. Tetrahedron Lett. 1980, 3849.
7. Cooke, M. P., Jr. J. Org. Chem. 1986, 51, 1637.
8. Cf. (a) Pinnick, H. W.; Fernandez, E. J. Org. Chem. 1979, 44, 2810. (b) Paquette, L. A.; Nelson, N. A. J. Org. Chem. 1962, 27, 2272. (c) Greenfield, H.; Friedel, R. A.; Orchin, M. J. Am. Chem. Soc. 1954, 76, 1258.
9. Sakurai, H.; Hosomi, K.; Hayashi, J. Org. Synth. 1984, 62, 86. The product of conjugate addition of an allylsilane to a ketone may be converted to a 1, 6-enyne via methodology of Negishi (Negishi, E.-I.; King, A. O.; Kilma, W. L.; Patterson, W.; Silveira, A., Jr. J. Org. Chem. 1980, 45, 2526).
10. E.g.; La Belle, B. E.; Knudsen, M. J.; Olmstead, M. M.; Hope, H.; Yanuck, M. D.; Schore, N. E. J. Org. Chem. 1985, 50, 5125. Review of the Pauson-Khand reaction: Pauson, P. L. In Organometallics in Organic Synthesis. Aspects of a Modern Interdisciplinary Field; A. de Meijere, H. tom Dieck, Eds.; Springer: Berlin, 1988; p 233.
11. Regiocontrol has been achieved in a limited number of intermolecular cases both sterically and electronically and via ligand control: (a) Sampath, V.; Lund, E. C.; Knudsen, M. J.; Olmstead, M. M.; Schore, N. E. J. Org. Chem. 1987, 52, 3595. (b) Khand, I. U.; Pauson, P. L.; Habib, M. J. A. J. Chem. Res. Miniprint 1978, 4418. (c) Krafft, M. E. J. Am. Chem. Soc. 1988, 110, 968.