A Samarium(II) Iodide Promoted Tandem Radical Cyclization. The Total Synthesis of (±)-Hypnophilin and the Formal Synthesis of (±)-Coriolin

Journal of the American Chemical Society

Volumn 110, Issue 15, 1988, Pages 5064-5067

  Fevig, Thomas L ^a   Elliott, Richard L ^a   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845280002     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00223a026     Document Type: Article

References (35)

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24. The products were identified by comparison with authentic samples prepared by the reduction of 2, 2, 5-trimethylcyclopentanone; Rei, M.-H. J. Org. Chem. 1978, 43, 2173.
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28. 2-promoted reactions between aldehydes or ketones and olefins have employed activated olefins (α, β-unsaturated esters) in the presence of proton donors.
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31. This reagent was prepared by a modification of the procedure kindly provided by Professor Hua. See, Hua, D. H.; Sinai-Zingde, G.; Venkataraman, S. J. Am. Chem. Soc. 1985, 107, 4088. Bromide 10 was prepared by standard silylation (TBS-C1, imidazole, DMF) of the corresponding bromo alcohol. See, Searles, S., Jr.; Nickerson, R. G.; Witsiepe, W. K. J. Org. Chem. 1959, 24, 1839.
32. The corresponding TMS dienol ether was highly prone to hydrolysis, and attempted oxidation of this substrate by a variety of methods (Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011. Reference 16.) invariably gave low yields (15-30%) of dienone accompanied by large amounts (40-60%) of starting enone.
33. A much more detailed study of this reaction has recently been described by Keck. Keck, G. E. Meeting of the American Chemical Society, New Orleans, LA., Aug 30-Sept 4, 1987. Abstract No. 144 of the Organic Division.
34. Theis, A. B.; Townsend, C. A. Synth. Commun. 1981, 11(2), 157.
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