Total Synthesis of (±)-3-Demethoxyerythratidinone: Demonstration of a Radical Cyclization Route to a Site Specific Enol Derivative

Journal of the American Chemical Society

Volumn 109, Issue 3, 1987, Pages 917-918

  Danishefsky, Samuel J ^a   Panek, James S ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845281738     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00237a057     Document Type: Article

References (13)

1. Department of Chemistry, Boston University, Boston, MA 02215.
2. Barton, D. H. R.; Gunatilaka, A. A. L.; Letcher, R. M.; Lobo, A. M. F. T.; Widdowson, D. A. J. Chem. Soc., Perkin Trans. 1 1971, 874. (b) For recent reviews on erythrina alkaloids, see: Chawla, A. S.; Jackson, A. H. Nat. Prod. Rep. 1984, 371. Dyke, S. F.; Quessy, S. N. In The Alkaloids: Chemistry and Physiology; Vol XVIII, chapt. 1, 1eds. Manske, R. H. F., Rodrigo, R. G. A., Eds.; Academic: New York, 1981; Vol. XVIII, Chapter 1.
3. Tsuda, Y.; Nakai, A.; Kazo, I.; Suzuki, F.; Haruna, M. Heterocycles 1984, 22, 1817.
4. Danishefsky, S. J.; Chacalamannil, S.; Uang, B. J. J. Org. Chem. 1982, 47, 2231. Danishefsy, S.; Taniyama, E.; Webb, R. R. Tetrahedron Lett. 1983, 24, 11. Danishefsy, S.; Taniyama, E., Heterocycles 1983, 24, 15.
5. For recent reviews concerning the use of free radical cyclizations in organic synthesis, see: Giese, B., Ed.; Tetrahedron Symposia-in-Print; Tetrahedron, 1985, 41 (19), 3887–4289. Hart, D. Science (Washington, D. C.) 1984. 223. 883.
6. Giese, B.; Horler, H.; Zwick, W. Tetrahedron Lett. 1982, 23, 531.
7. Stork, G.; Darling, S. D. J. Am. Chem. Soc. 1964, 86, 1761. (b) For a compilation of early studies in this area, see: House, H. O. Rec. Chem. Prog. 1967, 28. 99.
8. For recent reports which serve as precedents, see: (a) Padwa, A.; Nimmesgern, H.; Wong, G. S. K. Tetrahedron Lett. 1985, 26, 957. (b) Keck, G. E.; Enholm, E. J. Tetrahedron Lett. 1985, 26, 3311.
9. Tsuda has reported the carbomethoxy version of 10, see: Tsuda, Y.; Isobe, K.; Toda, J.; Taga, J. Heterocycl. 1976, 5, 157.
10. Ito. Y.: Hirao. T.: Saegusa, T. J. Org. Chem. 1978, 43, 1011.
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12. Burke, S. D.; Fobare, W. F.; Armistead, D. M. J. Org. Chem. 1982, 47, 3348.
13. Still, W. C. J. Am. Chem. Soc. 1978. 100. 1481.