Synthetic studies on the erythrina alkaloids. Preparation of (±)-2-epi-erythrinitol

Tetrahedron Letters

Volumn 40, Issue 38, 1999, Pages 6887-6890

  Rigby, James H ^a   Deur, Christopher ^a   Heeg, Mary Jane ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

Alkaloids; Heck reaction; Isocyanates

Indexed keywords

ERYTHRINA ALKALOID; ERYTHRITOL; ISOCYANIC ACID DERIVATIVE; NATURAL PRODUCT;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033578726     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01389-1     Document Type: Article

References (14)

1. For a recent review of the erythrina alkaloids, see: Tsuda, Y.; Sano, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1996; Vol. 48, pp. 249-337.
2. For some recent synthetic studies on erythrinan alkaloids, see: (a) Padwa, A.; Hennig, R.; Kappe, C. O.; Reyer, T. S. J. Org. Chem. 1998, 63, 1144.
3. (b) Toda, J.; Niimura, Y.; Takeda, K.; Sano, T.; Tsuda, Y. Chem. Pharm. Bull. 1998, 46, 906.
4. (c) Tsuda, Y.; Hasoi, S.; Ishida, K.; Sangai, M. Chem. Pharm. Bull 1994, 42, 204.
5. 4 sugar (erythritol): Corrigenda: Fitoterapia 1993, LXIV, 383.
6. Rigby, J. H.; Hughes, R. C.; Heeg, M. J. J. Am. Chem. Soc. 1995, 117, 7834.
7. For the development of alkyl isocyanides as ,1-dipole equivalents, see: (a) Rigby, J. H.; Qabar, M. J. Am. Chem. Soc. 1991, 113, 8975.
8. (b) Rigby, J. H.; Qabar, M.; Ahmed, G.; Hughes, R. C. Tetrahedron 1993, 49, 10219.
9. For other useful 1,1-dipole equivalents, see: (c) Rigby, J. H.; Cavezza, A.; Ahmed, G. J. Am. Chem. Soc. 1996, 118, 12848.
10. (d) Rigby, J. H.; Cavezza, A.; Heeg, M. J. J. Am. Chem. Soc. 1998, 120, 3664.
11. 13C NMR, IR, MS) and analytical (combustion analysis and/or HRMS) data in complete accord with the assigned structure.
12. Unfortunately, efforts to install the SEM protection earlier in the synthetic sequence proved to be problematic.
13. Barton, D. H. R.; McCombie, S. J. Chem. Soc., Perkin Trans. 1 1975, 1574.
14. Efforts to obtain an authentic sample of the natural product for purposes of comparison with our synthetic material were unsuccessful. Therefore, strictly speaking, one cannot exclude the possibility that natural erythrinitol, in fact, possesses a structure that is different from the one reported in the original paper.