Assignment of absolute configuration to SCH 351448 via total synthesis

Organic Letters

Volumn 10, Issue 14, 2008, Pages 3101-3104

  Cheung, Lael L ^a   Marumoto, Shinji ^a   Anderson, Christopher D ^a   Rychnovsky, Scott D ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BIOLOGICAL PRODUCT; LACTONE; SCH 351448;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; MICROMONOSPORA; STEREOISOMERISM; SYNTHESIS;

ALKENES; BIOLOGICAL PRODUCTS; CYCLIZATION; LACTONES; MICROMONOSPORA; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 52049101846     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8011474     Document Type: Article

References (40)

1. Hegde, V. R.; Puar, M. S.; Dai, P.; Patel, M.; Gullo, V. P.; Das, P. R.; Bond, R. W.; McPhail, A. T. Tetrahedron Lett. 2000, 41, 1351-1354.
2. (a) Brown, M. S.; Goldstein, J. L. Science 1986, 232, 34-47.
3. (b) Brown, M. S.; Goldstein, J. L. Cell 1997, 89, 331-340.
4. (a) Kang, E. J.; Cho, E. J.; Lee, Y. E.; Ji, M. K.; Shin, D. M.; Chung, Y. K.; Lee, E. J. Am. Chem. Soc. 2004, 126, 2680-2681.
5. (b) Kang, E. J.; Cho, E. J.; Ji, M. K.; Lee, Y. E.; Shin, D. M.; Choi, S. Y.; Chung, Y. K.; Kim, J.-S.; Kim, H.-J.; Lee, S.-G.; Lah, M. S.; Lee, E. J. Org. Chem. 2005, 70, 6321-6329.
6. Soltani, O.; De Brabander, J. K. Org. Lett. 2005, 7, 2791-2793.
7. Bolshakov, S.; Leighton, J. L. Org. Lett. 2005, 7, 3809-3812.
8. Crimmins, M. T.; Vanier, G. S. Org. Lett. 2006, 8, 2887-2890.
9. Backes, J. R.; Koert, U. Eur. J. Org. Chem. 2006, 2777-2785.
10. Chan, K.-P.; Ling, Y. H.; Loh, T.-P. Chem. Commun. 2007, 939-941.
11. Dolmetsch, R. E.; Pajvani, U.; Fife, K.; Spotts, J. M.; Greenberg, M. E. Science 2001, 294, 333-339.
12. (a) Kopecky, D. J.; Rychnovsky, S. D. J. Am. Chem. Soc. 2001, 123, 8420-8421.
13. (b) Patterson, B.; Marumoto, S.; Rychnovsky, S. D. Org. Lett. 2003, 5, 3163-3166.
14. (c) Patterson, B.; Rychnovsky, S. D. Synlett 2004, 543-545.
15. (d) Van Orden, L. J.; Patterson, B. D.; Rychnovsky, S. D. J. Org. Chem. 2007, 72, 5784-5793.
16. (e) Gesinski, M. R.; Van Orden, L. J.; Rychnovsky, S. D. Synlett 2008, 363-366.
17. Rychnovsky, S. D.; Hu, Y. Q.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271-7274.
18. For examples of ion-templated metathesis, see: (a) Mohr, B.; Weck, M.; Sauvage, J.-P.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1308-1310.
19. (b) Ng, K.-Y.; Cowley, A. R.; Beer, P. D. Chem. Commun. 2006, 3676-3678.
20. (c) Akine, S.; Kagiyama, S.; Nabeshima, T. Inorg. Chem. 2007, 46, 9525-9527.
21. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467-8468.
22. Wipf, P.; Graham, T. H. J. Am. Chem. Soc. 2004, 126, 15346-15347.
23. Takai, K.; Kunisada, Y.; Tachibana, Y.; Yamaji, N.; Nakatani, E. Bull. Chem. Soc. Jpn. 2004, 77, 1581-1586.
24. Fürstner, A.; Konetzki, I. Tetrahedron 1996, 52, 15071-15078.
25. (a) Dreher, S. D.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 341-342.
26. (b) La Cruz, T. E.; Rychnovsky, S. D. Org. Lett. 2005, 7, 1873-1875.
27. Bhat, K. S.; Brown, H. C. J. Am. Chem. 1986, 108, 5919-5923.
28. Bode, J. W.; Gauthier, D. R., Jr.; Carreira, E. M. Chem. Commun. 2001, 2560-2561.
29. Gurjar, M. K.; Krishna, L. M.; Reddy, B. S.; Chorghade, M. S. Synthesis 2000, 557-560.
30. +) by ES-MS. For references regarding NMR studies of calcium coordination complexes please see: (a) Chen, C.-S.; Wu, S.-H.; Wu, Y.-Y.; Fang, J.-M.; Wu, T. H. Org. Lett. 2007, 9, 2985-2988.
31. (b) Akine, S.; Taniguchi, T.; Nabeshima, T. J. Am. Chem. Soc. 2006, 128, 15765-15774.
32. (c) Akine, S.; Taniguchi, T.; Saiki, T.; Nabeshima, T. J. Am. Chem. Soc. 2005, 127, 540-541.
33. (d) Nabeshima, T.; Takahashi, T.; Hanami, T.; Kikuchi, A.; Kawabe, T.; Yano, Y. J. Org. Chem. 1998, 63, 3802-3803.
34. (a) Stewart, I. C.; Ung, T.; Pletnev, A. A.; Berlin, J. M.; Grubbs, R. H.; Schrodi, Y. Org. Lett. 2007, 9, 1589-1592.
35. (b) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179.
36. (c) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
37. (d) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
38. Hoye, T. R.; Jeffrey, C. S.; Tennakoon, M. A.; Wang, J.; Zhao, H. J. Am. Chem. Soc. 2004, 126, 10210-10211.
39. 3). Both of these rotations were obtained from newly acid-equilibrated samples (ref 1). The reported rotation of synthetic (+)-SCH 351448 has varied from +22.4 to +79.9.
40. CD spectra are provided in the Supporting Information.