Synthesis of Hydroxylated Pyrrolizidines Related to Alexine using Cycloaddition Reactions of Functionalized Cyclic Nitrones

Synlett

Volumn 1997, Issue 1, 1997, Pages 123-125

  Hall, Adrian ^a   Meldrum, Kevin P ^a   Therond, Patrick R ^a   Wightman, Richard H ^a  

^a HERIOT WATT UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002646847     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-695     Document Type: Article

References (34)

1. Synthesis of castanospermine and isomers: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045 and refs. therein; synthesis of hydroxylated indolizidines: Herczegh, P.; Kovács, I.; Sztaricskai, F. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lucacs, G., Ed.; Springer Verlag: Berlin, 1993; p. 751.
2. Synthesis of castanospermine and isomers: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045 and refs. therein; synthesis of hydroxylated indolizidines: Herczegh, P.; Kovács, I.; Sztaricskai, F. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lucacs, G., Ed.; Springer Verlag: Berlin, 1993; p. 751.
3. Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199.
4. Nash, R. J.; Fellows, L. E.; Dring, J. V.; Fleet, G. W. J.; Girdhar, A.; Ramsden, N. G.; Peach, J. M.; Hegarty, M. P.; Schofield, A. M. Phytochemistry 1990, 29, 111, and refs. therein.
5. Taylor, D. L.; Nash, R.; Fellows, L. E.; Kang, M.S.; Syms, A. S. Antiviral Chem. Chemother. 1992, 3, 273.
6. Nash, R. J.; Thomas, P. I.; Waigh, R. D.; Fleet, G. W. J.; Wormald, M. R.; Lilley, P. M. de Q.; Watkin, D. J. Tetrahedron Lett. 1994, 35, 7849.
7. For earlier work on the use of cycloadditions of such nitrones to prepare hydroxylated pyrrolizidines and indolizidines see: McCaig, A. E.; Wightman, R. H. Tetrahedron Lett. 1993, 34, 3939; Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, Z.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211; Cordero, F. M.; Cicchi, S.; Goti, A., Brandi, A. Tetrahedron Lett. 1994, 35, 949; Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem., 1995, 60, 4743; Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806; Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761.
8. For earlier work on the use of cycloadditions of such nitrones to prepare hydroxylated pyrrolizidines and indolizidines see: McCaig, A. E.; Wightman, R. H. Tetrahedron Lett. 1993, 34, 3939; Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, Z.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211; Cordero, F. M.; Cicchi, S.; Goti, A., Brandi, A. Tetrahedron Lett. 1994, 35, 949; Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem., 1995, 60, 4743; Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806; Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761.
9. For earlier work on the use of cycloadditions of such nitrones to prepare hydroxylated pyrrolizidines and indolizidines see: McCaig, A. E.; Wightman, R. H. Tetrahedron Lett. 1993, 34, 3939; Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, Z.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211; Cordero, F. M.; Cicchi, S.; Goti, A., Brandi, A. Tetrahedron Lett. 1994, 35, 949; Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem., 1995, 60, 4743; Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806; Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761.
10. For earlier work on the use of cycloadditions of such nitrones to prepare hydroxylated pyrrolizidines and indolizidines see: McCaig, A. E.; Wightman, R. H. Tetrahedron Lett. 1993, 34, 3939; Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, Z.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211; Cordero, F. M.; Cicchi, S.; Goti, A., Brandi, A. Tetrahedron Lett. 1994, 35, 949; Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem., 1995, 60, 4743; Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806; Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761.
11. For earlier work on the use of cycloadditions of such nitrones to prepare hydroxylated pyrrolizidines and indolizidines see: McCaig, A. E.; Wightman, R. H. Tetrahedron Lett. 1993, 34, 3939; Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, Z.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211; Cordero, F. M.; Cicchi, S.; Goti, A., Brandi, A. Tetrahedron Lett. 1994, 35, 949; Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem., 1995, 60, 4743; Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806; Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761.
12. For earlier work on the use of cycloadditions of such nitrones to prepare hydroxylated pyrrolizidines and indolizidines see: McCaig, A. E.; Wightman, R. H. Tetrahedron Lett. 1993, 34, 3939; Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, Z.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211; Cordero, F. M.; Cicchi, S.; Goti, A., Brandi, A. Tetrahedron Lett. 1994, 35, 949; Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem., 1995, 60, 4743; Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806; Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761.
13. For previous synthetic work on australine and its stereoisomers, see: Fleet, G. W. J.; Haraldsson, M.; Nash, R. J.; Fellows, L. E. Tetrahedron Lett. 1988, 29, 5441; Pearson, W. H.; Hines, J. V. Tetrahedron Lett. 1991, 32, 5513; Choi, S.; Bruce, I.; Fairbanks, A. J.; Fleet, G. W. J.; Jones, A. H.; Nash, R. J.; Fellows, L. E. Tetrahedron Lett. 1991, 32, 5517; Ikota, N, Tetrahedron Lett. 1992, 33, 2553.
14. For previous synthetic work on australine and its stereoisomers, see: Fleet, G. W. J.; Haraldsson, M.; Nash, R. J.; Fellows, L. E. Tetrahedron Lett. 1988, 29, 5441; Pearson, W. H.; Hines, J. V. Tetrahedron Lett. 1991, 32, 5513; Choi, S.; Bruce, I.; Fairbanks, A. J.; Fleet, G. W. J.; Jones, A. H.; Nash, R. J.; Fellows, L. E. Tetrahedron Lett. 1991, 32, 5517; Ikota, N, Tetrahedron Lett. 1992, 33, 2553.
15. For previous synthetic work on australine and its stereoisomers, see: Fleet, G. W. J.; Haraldsson, M.; Nash, R. J.; Fellows, L. E. Tetrahedron Lett. 1988, 29, 5441; Pearson, W. H.; Hines, J. V. Tetrahedron Lett. 1991, 32, 5513; Choi, S.; Bruce, I.; Fairbanks, A. J.; Fleet, G. W. J.; Jones, A. H.; Nash, R. J.; Fellows, L. E. Tetrahedron Lett. 1991, 32, 5517; Ikota, N, Tetrahedron Lett. 1992, 33, 2553.
16. For previous synthetic work on australine and its stereoisomers, see: Fleet, G. W. J.; Haraldsson, M.; Nash, R. J.; Fellows, L. E. Tetrahedron Lett. 1988, 29, 5441; Pearson, W. H.; Hines, J. V. Tetrahedron Lett. 1991, 32, 5513; Choi, S.; Bruce, I.; Fairbanks, A. J.; Fleet, G. W. J.; Jones, A. H.; Nash, R. J.; Fellows, L. E. Tetrahedron Lett. 1991, 32, 5517; Ikota, N, Tetrahedron Lett. 1992, 33, 2553.
17. Hughes, N. A.; Speakman, P. R. H. Carbohydr. Res. 1965, 1, 171.
18. 2OH), 62.7 and 69.3 (C-3, C-7a), 72.1 72.7 and 73.3 (C-1, C-2, C-6).
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25. Grigg, R.; Hadjisoteriou, M.; Kennewell, P.; Markandu, J. J. Chem. Soc., Chem. Commun. 1992, 1537; see also ref. 16 for later observations concerning the mechanism of such cyclizations.
26. Cyclizations using iodine (Grigg, R.; Hadjisoteriou, M.; Kennewell, P.; Markandu, J.; Thornton-Pett, M. J. Chem. Soc., Chem. Commun. 1993, 1340) gave two iodomethyl nitrones analogous to 19 and 20 (ratio 3:5), but in poorer combined yield.
27. Chamberlin, A. R.; Mulholland, R. L., Jr.; Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 672 and refs therein; see in particular: Nicotra, F.; Panza, L.; Ronchetti, F.; Toma, L. Tetrahedron Lett. 1984, 25, 5937; Freeman, F.; Robarge, K.D. Carbohydr. Res. 1985, 137, 89.
28. Chamberlin, A. R.; Mulholland, R. L., Jr.; Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 672 and refs therein; see in particular: Nicotra, F.; Panza, L.; Ronchetti, F.; Toma, L. Tetrahedron Lett. 1984, 25, 5937; Freeman, F.; Robarge, K.D. Carbohydr. Res. 1985, 137, 89.
29. Chamberlin, A. R.; Mulholland, R. L., Jr.; Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 672 and refs therein; see in particular: Nicotra, F.; Panza, L.; Ronchetti, F.; Toma, L. Tetrahedron Lett. 1984, 25, 5937; Freeman, F.; Robarge, K.D. Carbohydr. Res. 1985, 137, 89.
30. 3), 35.4 (C-7), 57.2 (C-5), 67.3 and 68.0 (C-3, C-7a), 71.5, 73.2 and 76.2 (C-1, C-2, C-6).
31. e.g. Ohrui, H.; Jones, G. H.; Moffatt, J. G.; Maddox, M. L.; Christensen, A. T.; Byram, S. K. J. Am. Chem. Soc. 1975, 97, 4602.
32. Additionally, very small amounts (∼1%) of a third cycloadduct were isolated to which the regioisomeric structure A is assigned by nmr. (Equation Presented) Cycloaddition of the cis-trans -nitrone 20 with allyl TBDPS ether gave two cycloadducts B and C (68% total yield), in a ratio of 4:3. (Equation Presented)
33. e.g. Curran, D. P. J. Am. Chem. Soc. 1982, 104, 4024.
34. Clive, D. L. J.; Chittattu, G. J.; Farina, V.; Kiel, W. A.; Menchen, S. M.; Russell, C. G.; Singh, A.; Wong, C. K.; Curtis, N. J. J. Am. Chem. Soc. 1980, 102, 4438.