Nonstabilized Imidate Ylides by the Desilylation Method: A Route to the Pyrrolizidine Alkaloids Retronecine and Indicine

Journal of Organic Chemistry

Volumn 50, Issue 12, 1985, Pages 2170-2174

  Vedejs, Edwin ^a   Larsen, Scott ^a   West, Frederick G ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001570148     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00212a034     Document Type: Article

References (12)

1. Reviews: (a) Lown, J. W. Recent Chem. Prog. 1971, 32, 51. (b) Kellogg, R. M. Tetrahedron 1976, 32, 2165. (c) Huisgen, R. J. Org. Chem. 1976, 41, 403. See also: Hermann, H.; Huisgen, R.; Mader, H. J. Am. Chem. Soc. 1971, 93, 1779 and references therein.
2. Deyrup, J. A.; Szabo, W. A. J. Org. Chem. 1975, 40, 2048. Deyrup, J. A.; Kuta, G. S. J. Org. Chem. 1978, 43, 501. Burger, K.; Meffert, A.; Bauer, S. J. Fluorine Chem. 1977, 10, 57. Beugelmans, R.; Negron, G.; Roussi, G. J. Chem. Soc., Chem. Commun. 1983, 31.
3. Vedejs, E.; Martinez, G. R. J. Am. Chem. Soc. 1979, 101, 6452.
4. Vedejs, E.; Martinez, G. R. J. Am. Chem. Soc. 1980, 102, 7993.
5. Vedejs, E.; West, F. G. J. Org. Chem. 1983, 48, 4773.
6. Achiwa, K.; Sekiya, M. Chem. Lett. 1981, 1213. Achiwa, K.; Sekiya, M. Tetrahedron Lett. 1982, 23, 2589. Teraro, Y.; Imai, N.; Achiwa, K., Sekiya, M. Chem. Pharm. Bull. 1983, 30, 3167. Chen, S.-F.; Ullrich, J. W.; Mariano, P. S. J. Am. Chem. Soc. 1983, 105, 6160. Padwa, A.; Chen, Y.-Y. Tetrahedron Lett. 1983, 24, 3447. Smith, R.; Livinghouse, T. J. Org. Chem. 1983, 48, 1554. Padwa, A.; Haffmanns, G.; Tomas, M. Tetrahedron Lett. 1983, 24, 4303.
7. (a) Mattocks, A. R.; Schoental, R.; Crowley, H. C.; Culvenor, C. C. J. J. Chem. Soc. 1961, 5400. Culvenor, C. C. J.; Smith, L. W. Aust. J. Chem. 1966, 19, 1955. (b) Indicine N-oxide as an antitumor agent: Powis, G.; Ames, M. M.; Kovach, J. S. Cancer Res. 1979, 39, 3564. Kovach, J. S.; Ames, M. M.; Powis, G.; Moertel, C. G.; Hahn, R. G.; Creagan, E. T. Cancer Res. 1979, 39, 4540.
8. For synthetic results on retronecine dilactones (fulvine, crispatine, etc.): Vedejs, E.; Larsen, S. D. J. Am. Chem. Soc. 1984, 106, 3030.
9. Ambasht, S.; Chin, S. K.; Peterson, P. E.; Queen, J. Synthesis 1980, 318. (10) Vedejs, E.; Engler, D. A.; Telschow, J. E. J. Org. Chem. 1978, 43, 188.
10. For analogous trapping of aluminum enolates generated by 1,4-addition of Dibal see: Itoh, A.; Ozawa, S.; Oshima, S.; Nozaki, H.Bull. Chem. Soc. Jpn. 1981, 54, 274.
11. (a) Geissman, T. A.; Weiss, A. C. J. Org. Chem. 1962, 27, 139. (b) Tufariello, J. J.; Lee, G. E. J. Am. Chem. Soc. 1980, 102, 373. (c) Keck, G. E.; Mickel, D. G. J. Am. Chem. Soc. 1980, 102, 3632. (d) Osawa, T. Ihara, M.; Fukumoto, K.; Kametani, T. Heterocycles 1982, 19, 2075: J. Org. Chem. 1983, 48, 3644. (e) Narasaka, K.; Sakakura, T.; Uchimura, T.; Morimoto, K.; Mukaiyama, T. Chem. Lett. 1982, 455. (f) Rueger, H.; Benn, M. Heterocycles 1983, 20, 1331. (g) Niwa, H.; Kuroda, A.; Yamada, K. Chem. Lett. 1983, 125.
12. Piper, J. R.; Kari, P.; Shealy, Y. F. J. Labelled Compd. Radiopharm. 1981, 18, 1579. (14) Kindly provided by Dr. A. R. Mattocks, Medical Research Council Laboratories, United Kingdom.