5-exo Radical cyclization onto 3-alkoxyketimino- 1,6-anhydromannopyranoses. Efficient preparation of synthetic intermediates for (-)-tetrodotoxin

Journal of Organic Chemistry

Volumn 65, Issue 19, 2000, Pages 5960-5968

  Noya, B ^a   Paredes, M D ^a   Ozores, L ^a   Alonso, R ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

3 ALKOXYKETIMINO 1,6 ANHYDROMANNOPYRANOSE DERIVATIVE; CARBOHYDRATE; MANNOSE; OXIME DERIVATIVE; RADICAL; TETRODOTOXIN; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

ALKYLATION; CYCLIZATION; MANNOSE; MOLECULAR CONFORMATION; MORPHOLINES; STEREOISOMERISM; TETRODOTOXIN; VINYL COMPOUNDS;

EID: 0034703414     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000325y     Document Type: Article

References (52)

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34. (a) Barlett, P. A.; McLaren, K. L.; Ting, P. C. J. Am. Chem. Soc. 1988, 110, 1633-1634. During our work the use of this transformation for the formation of bicyclo[2.2.1]heptanes was also reported:
35. (b) Della, E. W.; Knill, A. M. Aust. J. Chem. 1994, 47, 1833-1841. More recently, G. Fu and T. Naito have independently reported on the intramolecular addition of α-alkoxy alkyl radicals to form carbocycles and N-heterocycles, respectively:
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37. (d) Naito, T.; Nakagawa, K.; Nakamura, T.; Kasei, A.; Ninomiya, I.; Kiguchi, T. J. Org. Chem. 1999, 64, 2003-2009. For the intramolecular addition of vinyl and aryl radicals to ketoxime ethers see ref. 16.
38. Cis-fusion of the tetrahydrofuran ring in 6, (also in 19, 22a, 22b, 26, and 30) is assumed on the basis of numerous precedents in which exclusive formation of cis-fused bicyclic products in this type of radical cyclization has been reported. See for example Stork, G.; Mook, R.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741-3742. For 30, indirect proof of this stereochemical outcome comes from its successful transformation into 32.
39. Zottola, M. A.; Alonso, R. A.; Vite, G. D.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 6123-6125.
40. 3SnCl, NaBH4, hv, EtOH), which was first used by Corey for dehalogenation of organic halides: Corey, E. J.; Suggs, J. W. J. Org. Chem. 1975, 40, 2554-2555, and was later applied by Giese to the addition of radicals derived from alkyl iodides to electrophilic olefins: Giese, B.; González-Gómez J. A.; Witzel, T. Angew. Chem., Int. Ed. Engl. 1984, 23, 69-70 and Gerth, D. B.; Giese, B. J. Org. Chem. 1986, 51, 3726-3729.
41. 3SnCl, NaBH4, hv, EtOH), which was first used by Corey for dehalogenation of organic halides: Corey, E. J.; Suggs, J. W. J. Org. Chem. 1975, 40, 2554-2555, and was later applied by Giese to the addition of radicals derived from alkyl iodides to electrophilic olefins: Giese, B.; González-Gómez J. A.; Witzel, T. Angew. Chem., Int. Ed. Engl. 1984, 23, 69-70 and Gerth, D. B.; Giese, B. J. Org. Chem. 1986, 51, 3726-3729.
42. 3SnCl, NaBH4, hv, EtOH), which was first used by Corey for dehalogenation of organic halides: Corey, E. J.; Suggs, J. W. J. Org. Chem. 1975, 40, 2554-2555, and was later applied by Giese to the addition of radicals derived from alkyl iodides to electrophilic olefins: Giese, B.; González-Gómez J. A.; Witzel, T. Angew. Chem., Int. Ed. Engl. 1984, 23, 69-70 and Gerth, D. B.; Giese, B. J. Org. Chem. 1986, 51, 3726-3729.
43. See Supporting Information.
44. 2 carbon has been recently observed in the tosyl radical-mediated cyclization of β-allenyl ketoximebenzoates: Depature, M.; Siri, D.; Grimaldi, J.; Hatem, J. Tetrahedron Lett. 1999, 40, 4547-4550.
45. 3CN transformed iodoacetal 4 (1:1 diastereomeric mixture) into the corresponding morpholine (unpublished results). The reaction was again highly stereoselective, one diastereomer of 4 being cleanly converted to the morpholine and the other recovered unchanged.
46. α-Hydroxyketoxime ether 10 was obtained from ketone 9 as a single stereoisomer. Transformation of the iodoacetal 11 into morpholine 15 strongly supports the Z configuration for both 11 and its precursor 10.
47. See, for example Curran, D. P. Synthesis 1988, 428-430 and references therein.
48. Addition of vinyl radicals generated from alkynes to methyl ketoximes was first reported by Enholm: Enholm, E. J.; Burrof, J. A.; Jaramillo, L. M. Tetrahedron Lett. 1990, 31, 3727-3730. Use of aryl radicals was described by Jenkins: Booth, S. E.; Jenkins, P. R.; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. 1 1994, 3499-3508. For the special case of addition of vinyl radicals to ketoximes derived from cyclobutanone, see: Pattenden, G.; Schulz, D. Tetrahedron Lett. 1993, 34, 6787-6790 and Hollingworth, G. J.; Pattenden, G.; Schulz, D. J. Aust. J. Chem. 1995, 48, 8, 381. For a review of heteroatom radical addition-cyclization, see Naito, T. Heterocycles 1999, 50, 505-541.
49. Addition of vinyl radicals generated from alkynes to methyl ketoximes was first reported by Enholm: Enholm, E. J.; Burrof, J. A.; Jaramillo, L. M. Tetrahedron Lett. 1990, 31, 3727-3730. Use of aryl radicals was described by Jenkins: Booth, S. E.; Jenkins, P. R.; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. 1 1994, 3499-3508. For the special case of addition of vinyl radicals to ketoximes derived from cyclobutanone, see: Pattenden, G.; Schulz, D. Tetrahedron Lett. 1993, 34, 6787-6790 and Hollingworth, G. J.; Pattenden, G.; Schulz, D. J. Aust. J. Chem. 1995, 48, 8, 381. For a review of heteroatom radical addition-cyclization, see Naito, T. Heterocycles 1999, 50, 505-541.
50. Addition of vinyl radicals generated from alkynes to methyl ketoximes was first reported by Enholm: Enholm, E. J.; Burrof, J. A.; Jaramillo, L. M. Tetrahedron Lett. 1990, 31, 3727-3730. Use of aryl radicals was described by Jenkins: Booth, S. E.; Jenkins, P. R.; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. 1 1994, 3499-3508. For the special case of addition of vinyl radicals to ketoximes derived from cyclobutanone, see: Pattenden, G.; Schulz, D. Tetrahedron Lett. 1993, 34, 6787-6790 and Hollingworth, G. J.; Pattenden, G.; Schulz, D. J. Aust. J. Chem. 1995, 48, 8, 381. For a review of heteroatom radical addition-cyclization, see Naito, T. Heterocycles 1999, 50, 505-541.
51. Addition of vinyl radicals generated from alkynes to methyl ketoximes was first reported by Enholm: Enholm, E. J.; Burrof, J. A.; Jaramillo, L. M. Tetrahedron Lett. 1990, 31, 3727-3730. Use of aryl radicals was described by Jenkins: Booth, S. E.; Jenkins, P. R.; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. 1 1994, 3499-3508. For the special case of addition of vinyl radicals to ketoximes derived from cyclobutanone, see: Pattenden, G.; Schulz, D. Tetrahedron Lett. 1993, 34, 6787-6790 and Hollingworth, G. J.; Pattenden, G.; Schulz, D. J. Aust. J. Chem. 1995, 48, 8, 381. For a review of heteroatom radical addition-cyclization, see Naito, T. Heterocycles 1999, 50, 505-541.
52. Addition of vinyl radicals generated from alkynes to methyl ketoximes was first reported by Enholm: Enholm, E. J.; Burrof, J. A.; Jaramillo, L. M. Tetrahedron Lett. 1990, 31, 3727-3730. Use of aryl radicals was described by Jenkins: Booth, S. E.; Jenkins, P. R.; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. 1 1994, 3499-3508. For the special case of addition of vinyl radicals to ketoximes derived from cyclobutanone, see: Pattenden, G.; Schulz, D. Tetrahedron Lett. 1993, 34, 6787-6790 and Hollingworth, G. J.; Pattenden, G.; Schulz, D. J. Aust. J. Chem. 1995, 48, 8, 381. For a review of heteroatom radical addition-cyclization, see Naito, T. Heterocycles 1999, 50, 505-541.