Efficient Synthesis of (-)trans-Kumausyne via Tandem Intramolecular Alkoxycarbonylation-Lactonization

Journal of Organic Chemistry

Volumn 63, Issue 4, 1998, Pages 916-917

  Boukouvalas, John ^a   Fortier, Geneviève ^a   Radu, Ioan Iosif ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001036586     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972066r     Document Type: Article

References (29)

1. Suzuki, T.; Koizumi, K.; Suzuki, M.; Kurosawa, E. Chem. Lett. 1983, 1643-1644.
2. For synthetic studies in this area see: (a) Tonn, C. E.; Palazón, J. M.; Ruiz-Pérez, C.; Rodríguez, M. L.; Martín, V. S. Tetrahedron Lett. 1988, 29, 3149-3152. (b) Stuart, J. G.; Nicolas, K. M. Heterocycles 1991, 32, 949-963. (c) Andrey, O.; Landais, Y. Tetrahedron Lett. 1993, 34, 8435-8438. (d) Evans, P. A.; Roseman, J. D. Tetrahedron Lett. 1995, 36, 31-35. (e) Andrey, O.; Glanzmann, C.; Landais, Y.; Parra-Rapado, L. Tetrahedron 1997, 53, 2835-2854.
3. For synthetic studies in this area see: (a) Tonn, C. E.; Palazón, J. M.; Ruiz-Pérez, C.; Rodríguez, M. L.; Martín, V. S. Tetrahedron Lett. 1988, 29, 3149-3152. (b) Stuart, J. G.; Nicolas, K. M. Heterocycles 1991, 32, 949-963. (c) Andrey, O.; Landais, Y. Tetrahedron Lett. 1993, 34, 8435-8438. (d) Evans, P. A.; Roseman, J. D. Tetrahedron Lett. 1995, 36, 31-35. (e) Andrey, O.; Glanzmann, C.; Landais, Y.; Parra-Rapado, L. Tetrahedron 1997, 53, 2835-2854.
4. For synthetic studies in this area see: (a) Tonn, C. E.; Palazón, J. M.; Ruiz-Pérez, C.; Rodríguez, M. L.; Martín, V. S. Tetrahedron Lett. 1988, 29, 3149-3152. (b) Stuart, J. G.; Nicolas, K. M. Heterocycles 1991, 32, 949-963. (c) Andrey, O.; Landais, Y. Tetrahedron Lett. 1993, 34, 8435-8438. (d) Evans, P. A.; Roseman, J. D. Tetrahedron Lett. 1995, 36, 31-35. (e) Andrey, O.; Glanzmann, C.; Landais, Y.; Parra-Rapado, L. Tetrahedron 1997, 53, 2835-2854.
5. For synthetic studies in this area see: (a) Tonn, C. E.; Palazón, J. M.; Ruiz-Pérez, C.; Rodríguez, M. L.; Martín, V. S. Tetrahedron Lett. 1988, 29, 3149-3152. (b) Stuart, J. G.; Nicolas, K. M. Heterocycles 1991, 32, 949-963. (c) Andrey, O.; Landais, Y. Tetrahedron Lett. 1993, 34, 8435-8438. (d) Evans, P. A.; Roseman, J. D. Tetrahedron Lett. 1995, 36, 31-35. (e) Andrey, O.; Glanzmann, C.; Landais, Y.; Parra-Rapado, L. Tetrahedron 1997, 53, 2835-2854.
6. For synthetic studies in this area see: (a) Tonn, C. E.; Palazón, J. M.; Ruiz-Pérez, C.; Rodríguez, M. L.; Martín, V. S. Tetrahedron Lett. 1988, 29, 3149-3152. (b) Stuart, J. G.; Nicolas, K. M. Heterocycles 1991, 32, 949-963. (c) Andrey, O.; Landais, Y. Tetrahedron Lett. 1993, 34, 8435-8438. (d) Evans, P. A.; Roseman, J. D. Tetrahedron Lett. 1995, 36, 31-35. (e) Andrey, O.; Glanzmann, C.; Landais, Y.; Parra-Rapado, L. Tetrahedron 1997, 53, 2835-2854.
7. Brown, M. J.; Harrison, T.; Overman, L. E. J. Am. Chem. Soc. 1991, 113, 5378-5384.
8. Presented in parts at the 211th ACS National Meeting, New Orleans, LA, March 24-28, 1996 (ORGN 434), and the 78th CSC Conference and Exhibition, Guelph, Ontario, May 28-June 1, 1995 (OR6: 338).
9. Presented in parts at the 211th ACS National Meeting, New Orleans, LA, March 24-28, 1996 (ORGN 434), and the 78th CSC Conference and Exhibition, Guelph, Ontario, May 28-June 1, 1995 (OR6: 338).
10. Osumi, K.; Sugimura, H. Tetrahedron Lett. 1995, 36, 5789-5792.
11. Martín, T.; Soler, M. A.; Betancort, J. M.; Martín, V. S. J. Org. Chem. 1997, 62, 1570-1571.
12. Barrow, R. A.; Capon, R. J. Aust. J. Chem. 1990, 43, 895-911.
13. (a) Semmelhack, M. F.; Bodurow, C.; Baum, M. Tetrahedron Lett. 1984, 25, 3171-3174.
14. (b) Tamaru, Y.; Kobayashi, T.; Kawamura, S.; Ochiai, H.; Hojo, M.; Yoshida, Z. Tetrahedron Lett. 1985, 26, 3207-3210.
15. Evans, D. A.; Gauchet-Prunet, J. A.; Carreira, E. M.; Charette, A. B. J. Org. Chem. 1991, 56, 741-750 and references therein.
16. Saito, S.; Ishikawa, T.; Kuroda, A.; Koga, K.; Moriwake, T. Tetrahedron 1992, 48, 4067-4086.
17. Robinson, R. A.; Clark, J. S.; Holmes, A. B. J. Am. Chem. Soc. 1993, 115, 10400-10401.
18. 13C NMR. The elemental composition of new compounds was confirmed by C,H-microanalyses or HRMS.
19. Banfi, L.; Cascio, G.; Guanti, G.; Manghisi, E.; Narisano, E.; Riva, R. Tetrahedron 1994, 50, 11967-11982. See also: Wess, G.; Kesseler, K.; Baader, E.; Bartmann, W.; Beck, G.; Bergmann, A.; Jendralla, H.; Bock, K.; Holtzstein, G.; Kleine, H.; Schnierer, M. Tetrahedron Lett. 1990, 31, 2545-2548.
20. Banfi, L.; Cascio, G.; Guanti, G.; Manghisi, E.; Narisano, E.; Riva, R. Tetrahedron 1994, 50, 11967-11982. See also: Wess, G.; Kesseler, K.; Baader, E.; Bartmann, W.; Beck, G.; Bergmann, A.; Jendralla, H.; Bock, K.; Holtzstein, G.; Kleine, H.; Schnierer, M. Tetrahedron Lett. 1990, 31, 2545-2548.
21. (a) Levin, J. I.; Turos, E.; Weinreb, S. M. Synth. Commun. 1982, 12, 989-993.
22. (b) For an excellent review see: Sibi, M. P. Org. Prep. Proc. Int. 1993, 25, 15-40.
23. 2BOMe (cf. ref 9).
24. A substantially longer route to lactone 12 from L-arabinose (12 steps) and the transformation of 12 into (-)-1a and (-)-1b have been reported by Sugimura (ref 5).
25. Nicolaou, K. C.; Webber, S. E. J. Am. Chem. Soc. 1984, 106, 5734-5736. See also ref 5.
26. This reagent proved superior to TBAF for deprotecting 14; for similar observations see: Paquette, L. A.; Doherty, A. M.; Rayner, C. M. J. Am. Chem. Soc. 1992, 114, 3910-3926.
27. (a) Hooz, J.; Gilani, S. S. H. Can. J. Chem. 1968, 46, 86-87.
28. (b) Tsushima, K.; Murai, A. Tetrahedron Lett. 1992, 33, 4345-4348.
29. After submission of this manuscript, a 22-step synthesis of (-)-trans. kumausyne from D-xylose, which employs radical cyclization of a β-alkoxyacrylate as the key step, was reported by Lee: Lee, E.; Yoo, S.-K.; Cho, Y.-S.; Cheon, H.-S,; Chong, Y. H. Tetrahedron Lett. 1997, 38, 7757-7758.