Development of an approach to the synthesis of the plakortones

Tetrahedron Letters

Volumn 41, Issue 19, 2000, Pages 3567-3571

  Semmelhack, M F ^a   Shanmugam, Ponnusamy ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE TRIPHOSPHATASE (CALCIUM); LACTONE DERIVATIVE; PLAKORTONE; UNCLASSIFIED DRUG;

ARTICLE; CALCIUM TRANSPORT; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SARCOPLASMIC RETICULUM; SYNTHESIS;

EID: 0034611944     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00464-0     Document Type: Article

References (35)

1. (a) Semmelhack, M. F.; Zhang, N. J. Org. Chem. 1989, 54, 4483.
2. (b) Semmelhack, M. F.; Epa, W. R.; Cheung, A. W.-H.; Gu, Y.; Kim, C.; Zhang, N.; Lew, W. J. Am. Chem. Soc. 1994, 116, 7455.
3. Tamura, Y.; Kobayashi, T.; Kawamura, S.-I.; Ochiai, H.; Hojo, M.; Yoshida, Z.-I. Tetrahedron Lett. 1985, 26, 3207.
4. Hosokawa, T.; Murahashi, S.-I. Heterocycles 1992, 33, 1097.
5. Gracza, T.; Jager, V. Synthesis 1994, 1359.
6. Paddon-Jones, G. C.; Moore, C. J.; Brecknell, D. J.; König, W. A.; Kitching, W. Tetrahedron Lett. 1997, 38, 3479. See also: Bittner, C.; Burgo, A.; Murphy, P. J.; Sung, Chi. H.; Thornhill, A. J. Tetrahedron Lett. 1999, 40, 3455.
7. Paddon-Jones, G. C.; Moore, C. J.; Brecknell, D. J.; König, W. A.; Kitching, W. Tetrahedron Lett. 1997, 38, 3479. See also: Bittner, C.; Burgo, A.; Murphy, P. J.; Sung, Chi. H.; Thornhill, A. J. Tetrahedron Lett. 1999, 40, 3455.
8. Semmelhack, M. F.; Bodurow, C.; Baum, M. Tetrahedron Lett. 1984, 25, 3171.
9. See Refs. 1a, b and: (a) Semmelhack, M. F.; Kim, C.; Zhang, N.; Bodurow, C.; Sanner, M.; Doubler, W.; Meier, M. Pure App. Chem. 1990, 62, 2035.
10. (b) McCormick, M.; Monahan, R.; Soria, J.; Goldsmith, D.; Liotta, D. J. Org. Chem. 1989, 54, 4485.
11. (a) Patil, A. D.; Freyer, A. J.; Bean, M. F.; Carte, B. K.; Westley, J. W.; Johnson, R. K.; Lahouratate, P. Tetrahedron 1996, 52, 377.
12. (b) Coll, K. E.; Johnson Jr., R. G.; Mc Kenna, E. Biochemistry 1999, 38, 2444 and references cited therein.
13. Kobayashi, M.; Shoji, N.; Ohizumi, Y. Biochim. Biophys. Acta 1987, 903, 96.
14. Murayama, T.; Ohizumi, Y.; Nakamura, H.; Sasaki, T.; Kobayashi, J. Experimentia 1989, 898.
15. Paddon-Jones, G. C.; Hungerford, N. L.; Hayes, P.; Kitching, W. Org. Lett. 1999, 1, 1905.
16. For an overview, see: (a) Hegedus, L. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA; p. 190ff.
17. Gracza, T.; Hasenohrl, T.; Stahl, U.; Jager, V. Synthesis 1991, 1108.
18. Using the SYBYL program through MacSpartan Plus.
19. (a) Organ, M. G.; Murray, A. P. J. Org. Chem. 1997, 62, 1523.
20. (b) Kuehne, M. E.; Matson, P. A.; Bornmann, W. G. J. Org. Chem. 1991, 56, 513.
21. (c) Corey, E. J.; Venkateswaralu, A. J. Am. Chem. Soc. 1972, 94, 6190
22. (a) Seebach, D.; Corey, E. J. J. Org. Chem. 1975, 40, 231.
23. (b) Seebach, D.; Steinmuller, D. Angew. Chem., Int. Ed. Engl. 1968, 7, 619.
24. (c) Corey, E. J.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1965, 4, 1075.
25. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392.
26. +: calcd: 329.2149; found: 329.2149.
27. Available from Sigma-Aldrich Chemical Co.
28. Johnson, W. S.; Werthermann, L.; Bartlett, W. R.; Brockson, T. J.; Li, T.-T.; Faulkner, D. J.; Peterson, M. R. J. Am. Chem. Soc. 1970, 92, 741.
29. 1H NMR spectrum) in 78% yield.
30. (a) Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 2647.
31. (b) Piancatelli, G.; Scettri, A.; D′Auria, A. Synthesis 1982, 245.
32. (a) Julia, M.; Paris, J.-M. Tetrahedron Lett. 1973, 4833.
33. (b) Simpkins, N. S. Sulfones in Organic Synthesis; Pergamon Press: New York, 1993.
34. (a) Nakagawa, I.; Hata, T. Tetrahedron Lett. 1975, 1408.
35. (b) Reich, H. J.; Chow, F.; Peake, S. L. Synthesis 1978, 299.