Biomimetic-type synthesis of halogenated tetrahydrofurans from Laurencia. Total synthesis of trans-(+)-deacetylkumausyne

Journal of Organic Chemistry

Volumn 62, Issue 6, 1997, Pages 1570-1571

  Martín, Tomás ^a   Soler, Marcos A ^a   Betancort, Juan M ^a   Martin, Victor S ^a  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DEACETYLKUMAUSYNE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030939409     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962135m     Document Type: Article

References (24)

1. (a) Moore, R. E. In Marine Natural Products; Scheuer, P. J., Ed.; Academic Press: New York, 1978; Vol. 1, pp 43-121.
2. (b) Erickson, K. L. In Marine Natural Products; Scheuer, P. J., Ed.; Academic Press: New York, 1983; Vol. V, pp 131-257.
3. (c) Faulkner, D. J. Nat. Prod. Rep. 1984, 1, 251;
4. (d) 1986, 3, 1;
5. (e) 1987, 4, 539;
6. (f) 1988, 5, 613;
7. (g) 1990, 7, 269;
8. (h) 1991, 8, 97;
9. (i) 1992, 9, 323;
10. (j) 1993, 10, 497;
11. (k) 1994, 11, 355;
12. (l) 1995, 12, 223.
13. Suzuki, T.; Koizumi, K.; Suzuki, M.; Kurosawa, E. Chem. Lett. 1983, 1643.
14. Brown, M. J.; Harrison, T.; Overman, L. E. J. Am. Chem. Soc. 1991, 113, 5378.
15. Osumi, K.; Sugimura, H. Tetrahedron Lett. 1995, 36, 5789.
16. Tonn, C. E.; Palazón, J. M.; Ruiz-Pérez, C.; Rodríguez, M. L.; Martín, V. S. Tetrahedron Lett. 1988, 29, 3149.
17. Añorbe, B.; Martín, V. S. Unpublished results.
18. Añorbe, B.; Martín, V. S.; Palazón, J. M.; Trujillo, J. M. Tetrahedron Lett. 1986, 27, 4991.
19. Taber, D. F.; You, K. J. Org. Chem. 1995, 60, 139.
20. Palazón, J. M.; Añorbe, B.; Martín, V. S. Tetrahedron Lett. 1986, 27, 4987.
21. Yamaguchi, M.; Hirao, I. J. Chem. Soc., Chem. Commun. 1984, 202.
22. For the use of other reagents to promote the cyclization of hydroxyalkene to exo-bromotetrahydrofurans, see: Harding, K. E., Tiner, T. H. In Comprehensive Organic Synthesis; Trost, B. M., et al., Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 363-421.
23. The use of highly polar solvents such us THF:HMPTA yielded a poorer stereoselection of 10 relative to 11 (1:2). See ref 5.
24. Corey, E. J.; Ruden, R. A. Tetrahedron Lett. 1973, 1495.