Total synthesis of zoanthamine alkaloids, part 2. Construction of the C1-C5, C6-C10, and C11-C24 fragments of zoanthamine

Acta Chemica Scandinavica

Volumn 51, Issue 12, 1997, Pages 1217-1223

  Tanner, David ^a   Tedenborg, Lars ^b   Somfai, Peter ^c  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b UPPSALA UNIVERSITY   (Sweden)

^c LUND INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000269425     PISSN: 0904213X     EISSN: None     Source Type: Journal    
DOI: 10.3891/acta.chem.scand.51-1217     Document Type: Article

References (16)

1. Tanner, D., Andersson, P. G., Tedenborg, L. and Somfai, P. Tetrahedron 50 (1994) 9135.
2. Isolation and structure determination: Rao, C. B., Anjaneyulu, A. S. R., Sarma, N. S., Venkateswarlu, Y., Rosser, R. M., Faulkner, D. J., Chen, M. H. M. and Clardy, J. J. Am. Chem. Soc. 106 (1984) 7983.
3. (a) Hanessian, S. and Murray, P. J. Tetrahedron 43 (1987) 5055
4. (b) Hanessian, S., Roy, R. J., Petrini, M., Hodges, P. J., Di Fabio, R. and Carganico, G. J. Org. Chem. 55 (1990) 5766
5. (c) the spectral and physical data for our compound (except for the sign of optical rotation) were in agreement with those published for the enantiomer.
6. Tanner, D. and Tedenborg, L. Unpublished results.
7. Zhang, H. X., Guibé, F. and Balavoine, G. J. Org. Chem. 55 (1990) 1857.
8. Review: Ley, S. V., Norman, J., Griffith, W. P. and Marsden, S. P. Synthesis (1994) 639.
9. For related examples, see: (a) Spino, C., Liu, G., Tu, N. and Girard, S. J. Org. Chem. 59 (1994) 5596 (b) Danishefsky, S. and Bednarski, M. Tetrahedron Lett. 25 (1984) 721.
10. For related examples, see: (a) Spino, C., Liu, G., Tu, N. and Girard, S. J. Org. Chem. 59 (1994) 5596 (b) Danishefsky, S. and Bednarski, M. Tetrahedron Lett. 25 (1984) 721.
11. For stereoselective reactions of related alkynoate esters under carefully controlled conditions, see: (a) Piers, E. and Morton, H. E. J. Org. Chem. 45 (1980) 4263 (b) Piers, E., Chong, J. M. and Morton, H. E. Tetrahedron Lett. 22 (1981) 4905 (c) Cox, S. D. and Wudl, F. Organometallics 2 (1983) 184 (d) Pereira, O. Z. and Chan, T. H. Tetrahedron Lett. 36 (1995) 8749.
12. For stereoselective reactions of related alkynoate esters under carefully controlled conditions, see: (a) Piers, E. and Morton, H. E. J. Org. Chem. 45 (1980) 4263 (b) Piers, E., Chong, J. M. and Morton, H. E. Tetrahedron Lett. 22 (1981) 4905 (c) Cox, S. D. and Wudl, F. Organometallics 2 (1983) 184 (d) Pereira, O. Z. and Chan, T. H. Tetrahedron Lett. 36 (1995) 8749.
13. For stereoselective reactions of related alkynoate esters under carefully controlled conditions, see: (a) Piers, E. and Morton, H. E. J. Org. Chem. 45 (1980) 4263 (b) Piers, E., Chong, J. M. and Morton, H. E. Tetrahedron Lett. 22 (1981) 4905 (c) Cox, S. D. and Wudl, F. Organometallics 2 (1983) 184 (d) Pereira, O. Z. and Chan, T. H. Tetrahedron Lett. 36 (1995) 8749.
14. For stereoselective reactions of related alkynoate esters under carefully controlled conditions, see: (a) Piers, E. and Morton, H. E. J. Org. Chem. 45 (1980) 4263 (b) Piers, E., Chong, J. M. and Morton, H. E. Tetrahedron Lett. 22 (1981) 4905 (c) Cox, S. D. and Wudl, F. Organometallics 2 (1983) 184 (d) Pereira, O. Z. and Chan, T. H. Tetrahedron Lett. 36 (1995) 8749.
15. Stille, J. K. and Groh, B. L. J. Am. Chem. Soc. 109 (1987) 813.
16. Chaudhary, S. K. and Hernandez, O. Tetrahedron Lett. (1979) 99.