A mild new procedure for production, cyclization and trapping of amidyl radicals: Application to a formal total synthesis of peduncularine

Tetrahedron Letters

Volumn 41, Issue 14, 2000, Pages 2333-2337

  Lin, Xichen ^a   Stien, Didier ^a   Weinreb, Steven M ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

Alkaloids; Cyclization; Hydroxamic acids and derivatives; Nitrogen heterocycles; Radicals and radical reactions

Indexed keywords

ALKALOID; HYDROXAMIC ACID; NITROGEN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS; THERMODYNAMICS;

EID: 0034175611     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00194-5     Document Type: Article

References (23)

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3. For excellent reviews of the chemistry of nitrogen radicals see: (a) Esker, J. L.; Newcomb, M. Adv. Hetercycl. Chem. 1993, 58, 1. (b) Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17 543.
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11. For some recent notable examples of generating amidyl radicals from hydroxamic acid derivatives, see: (a) Boivin, J.; Callier-Dublanchet, A.-C.; Quiclet-Sire, B.; Schiano, A.-M.; Zard, S. Z. Tetrahedron 1995, 51, 6517. (b) Clark, A. J.; Filik, R. P.; Peacock, J. L.; Thomas, G. H. Synlett. 1999, 441. (c) Clark, A. J.; Deeth, R. J.; Samuel, C. J.; Wongtap, H. Synlett. 1999, 444, and references cited therein.
12. For some recent notable examples of generating amidyl radicals from hydroxamic acid derivatives, see: (a) Boivin, J.; Callier-Dublanchet, A.-C.; Quiclet-Sire, B.; Schiano, A.-M.; Zard, S. Z. Tetrahedron 1995, 51, 6517. (b) Clark, A. J.; Filik, R. P.; Peacock, J. L.; Thomas, G. H. Synlett. 1999, 441. (c) Clark, A. J.; Deeth, R. J.; Samuel, C. J.; Wongtap, H. Synlett. 1999, 444, and references cited therein.
13. For some recent notable examples of generating amidyl radicals from hydroxamic acid derivatives, see: (a) Boivin, J.; Callier-Dublanchet, A.-C.; Quiclet-Sire, B.; Schiano, A.-M.; Zard, S. Z. Tetrahedron 1995, 51, 6517. (b) Clark, A. J.; Filik, R. P.; Peacock, J. L.; Thomas, G. H. Synlett. 1999, 441. (c) Clark, A. J.; Deeth, R. J.; Samuel, C. J.; Wongtap, H. Synlett. 1999, 444, and references cited therein.
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15. Richey Jr., H. G.; Farkas Jr., J. J. Org. Chem. 1987, 52, 479. An alternative preparation of this sulfinyl chloride is available: Cogan, D. A.; Liu, G.; Kim, K.; Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 8011; Gontcharov, A. V.; Liu, H.; Sharpless, K. B. Org. Lett. 1999, 1, 783, and references cited therein.
16. Richey Jr., H. G.; Farkas Jr., J. J. Org. Chem. 1987, 52, 479. An alternative preparation of this sulfinyl chloride is available: Cogan, D. A.; Liu, G.; Kim, K.; Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 8011; Gontcharov, A. V.; Liu, H.; Sharpless, K. B. Org. Lett. 1999, 1, 783, and references cited therein.
17. Richey Jr., H. G.; Farkas Jr., J. J. Org. Chem. 1987, 52, 479. An alternative preparation of this sulfinyl chloride is available: Cogan, D. A.; Liu, G.; Kim, K.; Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 8011; Gontcharov, A. V.; Liu, H.; Sharpless, K. B. Org. Lett. 1999, 1, 783, and references cited therein.
18. General procedure for amidyl radical cyclizations: To a solution of the hydroxamic acid (0.3 mmol) and the radical trap (TEMPO: 0.45 mmol; diphenyl diselenide: 0.6 mmol; diphenyl disulfide: 12 mmol) in methylene chloride (15 mL) at -50°C was added N,N-diisopropylethylamine (0.75 mmol) and tert-butylsulfinyl chloride (0.45 mmol). The mixture was then warmed slowly to room temperature, and stirred for about 5 h. The solution was concentrated and the residue was purified by flash column chromatography on silica gel (hexanes:ethyl acetate, 80:20-50:50) to give the cyclization product.
19. For another example of a tandem amidyl radical cyclization see Ref. 7a.
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