Novel Photochemical-Diradical Cyclization Methods for Protoberberine Alkaloid Synthesis: Preparation of (±)-Xylopinine and (±)-Stylopine

Journal of Organic Chemistry

Volumn 52, Issue 4, 1987, Pages 704-706

  Dai Ho, Ginny ^a   Mariano, Patrick S ^a  

^a UNIVERSITY OF MARYLAND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 16044371033     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00380a048     Document Type: Letter

References (9)

1. Giese, B Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986, (2) Gilbert, A. In Synthetic Organic Photochemistry; Horspool, W. M., Ed.; Plenum Press: London, 1984; Chapter 1, pp 1–60. Weedon, A. C. Chapter 2, pp 61–144. (3) Mariano, P. S. Acc. Chem. Res. 1983, 16, 130. Mariano, P. S. In Synthetic Organic Photochemistry, Horspool, W. M. Ed.; Plenum Press: London, 1984; Chapter 3, pp 145–258. (4) Lan, A. J. Y.; Quillen, S. L.; Heuckeroth, R. O.; Mariano, P. S. J. Am. Chem. Soc. 1984, 106, 6439. (5) Dai-Ho, G.; Lan, A. J. Y.; Mariano, P. S. Tetrahedron Lett. 1985, 26, 5867.
2. For representative syntheses of xylopinine, see: (a) Bradsher, C. K.; Dutta, N. L. J. Org. Chem. 1961, 26, 2231. (b) Craig, L.,E., Tarbell, D. S. J. Am. Chem. Soc. 1948, 70, 2783. (c) Battersby, A. R.; LeCount, D. J.; Garratt, S.; Thrift, F. J. Tetrahedron 1961,14, 46. (d) Dyke, S. F.; Brown; D. W., Sainsbury, M.; Hardy, G. Tetrahedron 1971, 27, 3495. (e) Dutta, N. L.; Wadra, M. S.; Bundra, A. A. Ind. J. Chem. 1969, 7, 527. (f) Takano, S.; Numata, H.; Ogasawara, K. J. Chem. Soc. Chem. Commun. 1982, 769, (g) Dean, R. T.; Rapoport, H. J. Org. Chem. 1978, 43, 2217. (h) Meyers, A. T.; Boes, M.; Dickinson, D. A. Angew Chem., Int. Ed. Engl. 1984, 23, 458.
3. For representative syntheses of stylopine, see: (a) Haworth, R. D.; Perkin, W. H. J. Chem. Soc. 1926, 1769; and ref 6a.
4. Barthel, W. F.; Alexander, B. H. J. Org. Chem. 1958, 23, 1012.
5. Eaborn, G.; Walton, D. R. M.; Young, D. J. J. Chem. Soc. B 1969, 15.
6. (b) Buck, J. S.; Ide, W. S. J. Am. Chem. Soc. 1983, 60, 2101. (c) Decker, H.; Kropp, W.; Hayer, H.; Becker, P. Ann. 1913, 395, 299. (d) Whaley, W. M.; Govindachari, T. R. Organic Reactions; Wiley: New York, 1951; Vol. VI, Chapter 2.
7. Shamma, M.; Hindenlang, D. M. Carbon-13 NMR Shift Assignments of Amines and Alkaloids: Plenum: New York. 1979.
8. Pine. S. H.; Sanchez, B. L. J. Org. Chem. 1971. 36, 829.
9. Ranade, A. C.; Mall, R. S.; Bhide, S. R.; Metha, S. R. Synthesis 1976, 123.