New Methods for Alkaloid Synthesis: α-Acylamino Radical Cyclizations

Journal of the American Chemical Society

Volumn 104, Issue 5, 1982, Pages 1430-1432

  Hart, David J ^a   Tsai, Yeun Min ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845553580     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00369a050     Document Type: Article

References (25)

1. Dalton, D. R. “The Alkaloids”; Marcel Dekker: New York, 1979.
2. Seebach, D. Angew. Chem. Int. Ed. Engl. 1979, 18, 239 and references cited therein.
3. For a relevant synthesis of (±)-coniine see: Urry, W. H.; Juveland, O. O.; Stacey, F. W. J. Am. Chem. Soc. 1952, 74, 6155.
4. Urry, W. H.; Juveland, O. O. J. Am. Chem. Soc. 1958, 80, 3322.
5. For other brief accounts see: Julia, M.; Maumy, M. Bull. Soc. Chim. Fr. 1968, 1603.
6. Julia, M. Pure Appl. Chem. 1967, 15, 167.
7. For other methods of generating α-acylamino radicals see; Friedman, L.; Shechter, H. Tetrahedron Lett. 1961, 238.
8. Nikishin, G. I.; Mustafaev, R. I. Dokl. Akad. Nauk SSSR 1964, 158, 1127.
9. Elad, D.; Sinnreich, J. Tetrahedron 1968, 24, 4509.
10. Hubert, J. D.; Wijnberg, J. B. P. A.; Speckamp, W. N. Tetrahedron 1975, 31, 1437.
11. After the completion of this work, the method of α-acylamino radical generation independently developed herein was reported by others: Bachi, M. D.; Hoornaert, C. Tetrahedron Lett. 1981, 2693.
12. 1H NMR, mp, IR). Although (±)-pseudoheliotridane (12) was not isolated, the presence of small amounts of 8 in the cyclization mixture was apparent from NMR analyses of mixtures 7–9 and partially purified samples of 8 obtained by preparative gas chromatography.
13. For other syntheses of (±)-10 see: Weinreb, S. M.; Khatri, N. A.; Shringarpure, J. J. Am. Chem. Soc. 1979, 101, 5073 and references cited therein.
14. For other syntheses of 10 and 11 see: Miyano, S.; Fujii, S.; Yama-shita, O.; Toraishi, N.; Sumoto, K.; Satoh, F.; Masuda, T. J. Org. Chem. 1981, 46, 1737 and references cited therein.
15. For a summary of regiochemical guidelines for radical cyclizations see: Beckwith, A. L. J.; Easton, C. J.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 482.
16. For a relevant review see: Beckwith, A. L. J.; Ingold, K. U. In “Rearrangements in Ground and Excited States”; deMayo, P., Ed.; Academic Press: New York, 1980; Vol. 1, p 161;
17. For a recent example of a 5-hexen-1-yl type radical that undergoes an unusually large amount of endo cyclization see: Wilt, J. W. J. Am. Chem. Soc. 1981, 103, 5251.
18. Julia, M. Pure Appl. Chem. 1974, 40, 553.
19. Agosta W.C.; Wolff, S. J. Chem. Res. (C) 1981, 78.
20. For the effect of substituents on the regiochemical course of simple hexenyl radicals see: Julia, M.; Descoins, C.; Baillarge, M.; Jacquet, B.; Uguen, D.; Groeger, F. A. Tetrahedron 1975, 31, 1737.
21. Beckwith, A. L. J.; Phillipou, G.; Blair, I. A. Tetrahedron Lett. 1974, 2251.
22. Hart, D. J. J. Org. Chem. 1981, 46, 3576.
23. Hart, D. J. J. Am. Chem. Soc. 1980, 102, 397.
24. Hart, D. J. J. Org. Chem. 1981, 46, 367.
25. For an overview see: Robins, D. J. In “Advances in Heterocyclic Chemistry”; Katritzky, A. R., Boulton, A. J., Eds.; Academic Press: New York, 1979; Vol. 24, p 247.