Efficient formal synthesis of the dendrobatid alkaloid, indolizidine (-)-209B

Tetrahedron Asymmetry

Volumn 13, Issue 20, 2002, Pages 2257-2260

  Ma, Dawei ^a   Pu, Xiaotao ^a   Wang, Jinyi ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; BROMINE DERIVATIVE; ESTER DERIVATIVE; INDOLIZIDINE ALKALOID; PHOSPHORUS DERIVATIVE; PIPERIDINE DERIVATIVE; URETHAN;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; HYDROGENATION; POLYMERIZATION; PRIORITY JOURNAL;

EID: 0037131652     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00577-3     Document Type: Article

References (18)

1. For a review, see: Daly, J. W.; Garraffo, H. M.; Spande, T. F. In Alkaloids: Chemical & Biological Perspectives; Pelletier, S. W., Ed.; Pergamon Press: Oxford, 1999; Vol. 13; pp. 1-161.
2. Daly J.W., Nishizawa Y., Padgett W.L., Tokuyama T., Smith A.L., Holmes A.B., Kibayashi C., Aronstam R.S. Neurochem. Res. 16:1991;1213.
3. For recent studies, see: (a) Shu, C.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477; (b) Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543; (c) Michael, J. P.; Gravestock, D. J. Chem. Soc., Perkin Trans. 1 2000, 1919; (d) Bardou, A.; Celerier, J.-P.; Lhommet, G. Tetrahedron Lett. 1998, 39, 5189; (e) Comins, D. L.; LaMunyon, D. H.; Chen, X. J. Org. Chem. 1997, 62, 8182 and references cited therein. For the first synthesis of enantiopure (-)-indolizidine 209B, see: (f) Simth, A. L.; Williams, S. F.; Holmes, A. B.; Hughes, L. R.; Swithenbank, C.; Lidert, Z. J. Am. Chem. Soc. 1988, 110, 8696.
4. For recent studies, see: (a) Shu, C.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477; (b) Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543; (c) Michael, J. P.; Gravestock, D. J. Chem. Soc., Perkin Trans. 1 2000, 1919; (d) Bardou, A.; Celerier, J.-P.; Lhommet, G. Tetrahedron Lett. 1998, 39, 5189; (e) Comins, D. L.; LaMunyon, D. H.; Chen, X. J. Org. Chem. 1997, 62, 8182 and references cited therein. For the first synthesis of enantiopure (-)-indolizidine 209B, see: (f) Simth, A. L.; Williams, S. F.; Holmes, A. B.; Hughes, L. R.; Swithenbank, C.; Lidert, Z. J. Am. Chem. Soc. 1988, 110, 8696.
5. For recent studies, see: (a) Shu, C.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477; (b) Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543; (c) Michael, J. P.; Gravestock, D. J. Chem. Soc., Perkin Trans. 1 2000, 1919; (d) Bardou, A.; Celerier, J.-P.; Lhommet, G. Tetrahedron Lett. 1998, 39, 5189; (e) Comins, D. L.; LaMunyon, D. H.; Chen, X. J. Org. Chem. 1997, 62, 8182 and references cited therein. For the first synthesis of enantiopure (-)-indolizidine 209B, see: (f) Simth, A. L.; Williams, S. F.; Holmes, A. B.; Hughes, L. R.; Swithenbank, C.; Lidert, Z. J. Am. Chem. Soc. 1988, 110, 8696.
6. For recent studies, see: (a) Shu, C.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477; (b) Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543; (c) Michael, J. P.; Gravestock, D. J. Chem. Soc., Perkin Trans. 1 2000, 1919; (d) Bardou, A.; Celerier, J.-P.; Lhommet, G. Tetrahedron Lett. 1998, 39, 5189; (e) Comins, D. L.; LaMunyon, D. H.; Chen, X. J. Org. Chem. 1997, 62, 8182 and references cited therein. For the first synthesis of enantiopure (-)-indolizidine 209B, see: (f) Simth, A. L.; Williams, S. F.; Holmes, A. B.; Hughes, L. R.; Swithenbank, C.; Lidert, Z. J. Am. Chem. Soc. 1988, 110, 8696.
7. For recent studies, see: (a) Shu, C.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477; (b) Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543; (c) Michael, J. P.; Gravestock, D. J. Chem. Soc., Perkin Trans. 1 2000, 1919; (d) Bardou, A.; Celerier, J.-P.; Lhommet, G. Tetrahedron Lett. 1998, 39, 5189; (e) Comins, D. L.; LaMunyon, D. H.; Chen, X. J. Org. Chem. 1997, 62, 8182 and references cited therein. For the first synthesis of enantiopure (-)-indolizidine 209B, see: (f) Simth, A. L.; Williams, S. F.; Holmes, A. B.; Hughes, L. R.; Swithenbank, C.; Lidert, Z. J. Am. Chem. Soc. 1988, 110, 8696.
8. For recent studies, see: (a) Shu, C.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477; (b) Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543; (c) Michael, J. P.; Gravestock, D. J. Chem. Soc., Perkin Trans. 1 2000, 1919; (d) Bardou, A.; Celerier, J.-P.; Lhommet, G. Tetrahedron Lett. 1998, 39, 5189; (e) Comins, D. L.; LaMunyon, D. H.; Chen, X. J. Org. Chem. 1997, 62, 8182 and references cited therein. For the first synthesis of enantiopure (-)-indolizidine 209B, see: (f) Simth, A. L.; Williams, S. F.; Holmes, A. B.; Hughes, L. R.; Swithenbank, C.; Lidert, Z. J. Am. Chem. Soc. 1988, 110, 8696.
9. For other efforts on the synthesis of natural alkaloids from enantiopure β-amino esters from this group, see: (a) Ma, D.; Zhu, W. Org. Lett. 2001, 3, 3927; (b) Ma, D.; Xia, C.; Jiang, J.; Zhang, J. Org. Lett. 2001, 3, 2189; (c) Wang, Y.; Ma, D. Tetrahedron: Asymmetry 2001, 12, 725; (d) Ma, D.; Sun, H. J. Org. Chem. 2000, 65, 6009; (e) Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503; (f) Ma, D.; Sun, H. Tetrahedron Lett. 2000, 41, 1947; (g) Ma, D.; Sun, H. Tetrahedron Lett. 1999, 40, 3609; (h) Ma, D.; Zhang, J. Tetrahedron Lett. 1998, 39, 9067.
10. For other efforts on the synthesis of natural alkaloids from enantiopure β-amino esters from this group, see: (a) Ma, D.; Zhu, W. Org. Lett. 2001, 3, 3927; (b) Ma, D.; Xia, C.; Jiang, J.; Zhang, J. Org. Lett. 2001, 3, 2189; (c) Wang, Y.; Ma, D. Tetrahedron: Asymmetry 2001, 12, 725; (d) Ma, D.; Sun, H. J. Org. Chem. 2000, 65, 6009; (e) Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503; (f) Ma, D.; Sun, H. Tetrahedron Lett. 2000, 41, 1947; (g) Ma, D.; Sun, H. Tetrahedron Lett. 1999, 40, 3609; (h) Ma, D.; Zhang, J. Tetrahedron Lett. 1998, 39, 9067.
11. For other efforts on the synthesis of natural alkaloids from enantiopure β-amino esters from this group, see: (a) Ma, D.; Zhu, W. Org. Lett. 2001, 3, 3927; (b) Ma, D.; Xia, C.; Jiang, J.; Zhang, J. Org. Lett. 2001, 3, 2189; (c) Wang, Y.; Ma, D. Tetrahedron: Asymmetry 2001, 12, 725; (d) Ma, D.; Sun, H. J. Org. Chem. 2000, 65, 6009; (e) Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503; (f) Ma, D.; Sun, H. Tetrahedron Lett. 2000, 41, 1947; (g) Ma, D.; Sun, H. Tetrahedron Lett. 1999, 40, 3609; (h) Ma, D.; Zhang, J. Tetrahedron Lett. 1998, 39, 9067.
12. For other efforts on the synthesis of natural alkaloids from enantiopure β-amino esters from this group, see: (a) Ma, D.; Zhu, W. Org. Lett. 2001, 3, 3927; (b) Ma, D.; Xia, C.; Jiang, J.; Zhang, J. Org. Lett. 2001, 3, 2189; (c) Wang, Y.; Ma, D. Tetrahedron: Asymmetry 2001, 12, 725; (d) Ma, D.; Sun, H. J. Org. Chem. 2000, 65, 6009; (e) Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503; (f) Ma, D.; Sun, H. Tetrahedron Lett. 2000, 41, 1947; (g) Ma, D.; Sun, H. Tetrahedron Lett. 1999, 40, 3609; (h) Ma, D.; Zhang, J. Tetrahedron Lett. 1998, 39, 9067.
13. For other efforts on the synthesis of natural alkaloids from enantiopure β-amino esters from this group, see: (a) Ma, D.; Zhu, W. Org. Lett. 2001, 3, 3927; (b) Ma, D.; Xia, C.; Jiang, J.; Zhang, J. Org. Lett. 2001, 3, 2189; (c) Wang, Y.; Ma, D. Tetrahedron: Asymmetry 2001, 12, 725; (d) Ma, D.; Sun, H. J. Org. Chem. 2000, 65, 6009; (e) Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503; (f) Ma, D.; Sun, H. Tetrahedron Lett. 2000, 41, 1947; (g) Ma, D.; Sun, H. Tetrahedron Lett. 1999, 40, 3609; (h) Ma, D.; Zhang, J. Tetrahedron Lett. 1998, 39, 9067.
14. For other efforts on the synthesis of natural alkaloids from enantiopure β-amino esters from this group, see: (a) Ma, D.; Zhu, W. Org. Lett. 2001, 3, 3927; (b) Ma, D.; Xia, C.; Jiang, J.; Zhang, J. Org. Lett. 2001, 3, 2189; (c) Wang, Y.; Ma, D. Tetrahedron: Asymmetry 2001, 12, 725; (d) Ma, D.; Sun, H. J. Org. Chem. 2000, 65, 6009; (e) Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503; (f) Ma, D.; Sun, H. Tetrahedron Lett. 2000, 41, 1947; (g) Ma, D.; Sun, H. Tetrahedron Lett. 1999, 40, 3609; (h) Ma, D.; Zhang, J. Tetrahedron Lett. 1998, 39, 9067.
15. For other efforts on the synthesis of natural alkaloids from enantiopure β-amino esters from this group, see: (a) Ma, D.; Zhu, W. Org. Lett. 2001, 3, 3927; (b) Ma, D.; Xia, C.; Jiang, J.; Zhang, J. Org. Lett. 2001, 3, 2189; (c) Wang, Y.; Ma, D. Tetrahedron: Asymmetry 2001, 12, 725; (d) Ma, D.; Sun, H. J. Org. Chem. 2000, 65, 6009; (e) Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503; (f) Ma, D.; Sun, H. Tetrahedron Lett. 2000, 41, 1947; (g) Ma, D.; Sun, H. Tetrahedron Lett. 1999, 40, 3609; (h) Ma, D.; Zhang, J. Tetrahedron Lett. 1998, 39, 9067.
16. For other efforts on the synthesis of natural alkaloids from enantiopure β-amino esters from this group, see: (a) Ma, D.; Zhu, W. Org. Lett. 2001, 3, 3927; (b) Ma, D.; Xia, C.; Jiang, J.; Zhang, J. Org. Lett. 2001, 3, 2189; (c) Wang, Y.; Ma, D. Tetrahedron: Asymmetry 2001, 12, 725; (d) Ma, D.; Sun, H. J. Org. Chem. 2000, 65, 6009; (e) Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503; (f) Ma, D.; Sun, H. Tetrahedron Lett. 2000, 41, 1947; (g) Ma, D.; Sun, H. Tetrahedron Lett. 1999, 40, 3609; (h) Ma, D.; Zhang, J. Tetrahedron Lett. 1998, 39, 9067.
17. Davies S.G., Ichihara O. Tetrahedron: Asymmetry. 2:1991;183.
18. Paulvannan K., Stille J.R. J. Org. Chem. 59:1994;1613.