Synthesis of trihydroxylated pyrrolizidines and indolizidines using cycloaddition reactions of functionalized cyclic nitrones, and the synthesis of (+)- and (-)-lentiginosine

Tetrahedron

Volumn 54, Issue 32, 1998, Pages 9429-9446

  McCaig, Avril E ^a   Meldrum, Kevin P ^a   Wightman, Richard H ^a  

^a HERIOT WATT UNIVERSITY   (United Kingdom)

Author keywords

Alkaloids; Cycloadditions; Indolizidines; Pyrrolizidines

Indexed keywords

1,2,6 TRIHYDROXYPYRROLIZIDINE; 1,2,6 TRIHYDROXYPYRROLIZIDINE TRIFLUOROACETIC ACID; 1,2,7 TRIHYDROXYINDOLIZIDINE; 3,4 BIS(METHOXY METHOXY) DELTA1 PYRROLINE N OXIDE; 3,4 ISOPROPYLIDENE DELTA1 PYRROLINE 1 OXIDE; ALKENE; INDOLIZIDINE DERIVATIVE; LENTIGINOSINE; PYRROLINE DERIVATIVE; PYRROLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0032490930     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00572-9     Document Type: Article

References (45)

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10. 6. 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; Michael, J.P. Nat. Prod. Rep. 1997, 14, 619, and earlier reviews in that series; syntheses of swainsonine: Pearson, W.H.; Hembre, E.J. J. Org. Chem. 1996, 61, 7217, and refs. therein; synthetic work on australine and its stereoisomers: 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.
11. 6. 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; Michael, J.P. Nat. Prod. Rep. 1997, 14, 619, and earlier reviews in that series; syntheses of swainsonine: Pearson, W.H.; Hembre, E.J. J. Org. Chem. 1996, 61, 7217, and refs. therein; synthetic work on australine and its stereoisomers: 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.
12. 6. 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; Michael, J.P. Nat. Prod. Rep. 1997, 14, 619, and earlier reviews in that series; syntheses of swainsonine: Pearson, W.H.; Hembre, E.J. J. Org. Chem. 1996, 61, 7217, and refs. therein; synthetic work on australine and its stereoisomers: 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.
13. 6. 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; Michael, J.P. Nat. Prod. Rep. 1997, 14, 619, and earlier reviews in that series; syntheses of swainsonine: Pearson, W.H.; Hembre, E.J. J. Org. Chem. 1996, 61, 7217, and refs. therein; synthetic work on australine and its stereoisomers: 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. 6. 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; Michael, J.P. Nat. Prod. Rep. 1997, 14, 619, and earlier reviews in that series; syntheses of swainsonine: Pearson, W.H.; Hembre, E.J. J. Org. Chem. 1996, 61, 7217, and refs. therein; synthetic work on australine and its stereoisomers: 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. 6. 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; Michael, J.P. Nat. Prod. Rep. 1997, 14, 619, and earlier reviews in that series; syntheses of swainsonine: Pearson, W.H.; Hembre, E.J. J. Org. Chem. 1996, 61, 7217, and refs. therein; synthetic work on australine and its stereoisomers: 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. 6. 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; Michael, J.P. Nat. Prod. Rep. 1997, 14, 619, and earlier reviews in that series; syntheses of swainsonine: Pearson, W.H.; Hembre, E.J. J. Org. Chem. 1996, 61, 7217, and refs. therein; synthetic work on australine and its stereoisomers: 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.
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34. 21. A similar preparation of 26 and 27 from L-tartaric acid, and the oxidation of 27 to 28 was reported during the course of our work: Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316.
35. 22. Other workers have subsequently reported the preparation and use in cycloadditions of nitrones related to 28 with different protecting groups on oxygen: (a) Tbdps ether: Brandi, A; Cicchi, S.; Goti, A.; Koprowski, M.; Pietrusiewicz, K.M. J. Org. Chem. 1994, 59, 1315;
36. (b) Tbdms ether: Goti, A.; Cardona, F.; Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymm. 1996, 7, 1659; benzyl and t-butyl ethers: Cicchi, S.; Höld, I.; Brandi, A. J. Org. Chem. 1993, 58, 5274.
37. (b) Tbdms ether: Goti, A.; Cardona, F.; Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymm. 1996, 7, 1659; benzyl and t-butyl ethers: Cicchi, S.; Höld, I.; Brandi, A. J. Org. Chem. 1993, 58, 5274.
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40. 25. Yoda, H.; Kitayama, H.; Katagiri, T.; Takabe, K. Tetrahedron: Asymm. 1993, 4, 1455; Cordero, F.M.; Cicchi, S.; Goti, A; Brandi, A. Tetrahedron Lett. 1994, 35, 949; Gurjar, M.J.; Ghosh, L.; Syamala, M.; Jayasree, V. Tetrahedron Lett. 1994, 35, 8871; Giovannini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1995, 60, 5706.
41. 25. Yoda, H.; Kitayama, H.; Katagiri, T.; Takabe, K. Tetrahedron: Asymm. 1993, 4, 1455; Cordero, F.M.; Cicchi, S.; Goti, A; Brandi, A. Tetrahedron Lett. 1994, 35, 949; Gurjar, M.J.; Ghosh, L.; Syamala, M.; Jayasree, V. Tetrahedron Lett. 1994, 35, 8871; Giovannini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1995, 60, 5706.
42. 25. Yoda, H.; Kitayama, H.; Katagiri, T.; Takabe, K. Tetrahedron: Asymm. 1993, 4, 1455; Cordero, F.M.; Cicchi, S.; Goti, A; Brandi, A. Tetrahedron Lett. 1994, 35, 949; Gurjar, M.J.; Ghosh, L.; Syamala, M.; Jayasree, V. Tetrahedron Lett. 1994, 35, 8871; Giovannini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1995, 60, 5706.
43. 25. Yoda, H.; Kitayama, H.; Katagiri, T.; Takabe, K. Tetrahedron: Asymm. 1993, 4, 1455; Cordero, F.M.; Cicchi, S.; Goti, A; Brandi, A. Tetrahedron Lett. 1994, 35, 949; Gurjar, M.J.; Ghosh, L.; Syamala, M.; Jayasree, V. Tetrahedron Lett. 1994, 35, 8871; Giovannini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1995, 60, 5706.
44. 26. Brandi, A; Cicchi, S.; Cordero, F.M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806.
45. 27. Recently, a synthesis of (+)-lentiginosine has been described briefly, which involves the synthesis of the t-butyl-protected analogue of 38, made via cycloaddition of the nitrone to homoallyl alcohol: Goti, A.; Cardona, F.; Brandi, A. Synlett, 1996, 761.