A Biogenetic Approach to Halicholactones. Anomalous Cyclization of an Epoxytridecadienoic Acid

Synlett

Volumn 1996, Issue 1, 1996, Pages 31-33

  White, James D ^a   Jensen, Mark S ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343028958     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5327     Document Type: Article

References (16)

1. White, J. D.; Jensen, M. S. J. Am. Chem. Soc. 1995, 117, 6224.
2. White, J. D.; Jensen, M. S. J. Am. Chem. Soc. 1993, 115, 2970.
3. Baertschi, S. W.; Brash, A. R.; Harris, T. M. J. Am. Chem. Soc. 1989, 111, 5003.
4. (a) Niwa, H.; Wakamatsu, K.; Yamada, K. Tetrahedron Lett. 1989, 30, 4543.
5. (b) Kigoshi, H.; Niwa, H.; Yamada, K.; Stout, T. J.; Clardy, J. Tetrahedron Lett. 1991, 32, 2427.
6. The first syntheses of 6 and 7 were reported recently (Critcher, D. J.; Connolly, S.; Wills, M. Tetrahedron Lett. 1995, 36, 3763) and confirm the absolute configuration assigned by Yamada (ref 4). A proposed revision of the absolute configuration of 7 (Proteau, P. J.; Rossi, J. V., Gerwick, W. H. J. Nat. Prod. 1994, 57, 1717) has been found to be in error.
7. The first syntheses of 6 and 7 were reported recently (Critcher, D. J.; Connolly, S.; Wills, M. Tetrahedron Lett. 1995, 36, 3763) and confirm the absolute configuration assigned by Yamada (ref 4). A proposed revision of the absolute configuration of 7 (Proteau, P. J.; Rossi, J. V., Gerwick, W. H. J. Nat. Prod. 1994, 57, 1717) has been found to be in error.
8. Fallis, A. G.; Hearn, M. T. W.; Jones, E. R. H.; Thaller, V.; Turner, J. L. J. Chem. Soc., Perkin Trans. I 1973, 743.
9. Gannett, P. M.; Nagel, D. L.; Reilley, P. J.; Lawson, T.; Sharpe, J.; Toth, B. J. Org. Chem. 1988, 53, 1064.
10. Cf. Labelle, M.; Falgueyret, J.-P.; Riendeau, D.; Rokach, J. Tetrahedron 1990, 46, 6301.
11. Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5585.
12. Leusink, A. J.; Budding, H. A.; Drenth, W. J. Organomet. Chem. 1968, 11, 541 and preceding papers.
13. Echavarren, A. M.; Tueting, D. R.; Stille, J. K. J. Am. Chem. Soc. 1988, 110, 4039.
14. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc, 1987, 109, 5765.
15. Conditions for this transformation are as specified in ref. 1.
16. For a review of inverse-detection two-dimensional NMR methods see: Martin, G. E.; Crouch, R. C. J. Nat. Prod. 1991, 54, 1.