Synthesis of the C3-C19 segment of phorboxazole B

Organic Letters

Volumn 7, Issue 15, 2005, Pages 3255-3258

  Vitale, Justin P ^a   Wolckenhauer, Scott A ^a   Do, Nga M ^a   Rychnovsky, Scott D ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FUSED HETEROCYCLIC RINGS; OXAZOLE DERIVATIVE; PHORBOXAZOLE A;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SPONGE (PORIFERA); SYNTHESIS;

ANIMALS; CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MOLECULAR STRUCTURE; OXAZOLES; PORIFERA;

EID: 23044499887     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051039h     Document Type: Article

References (47)

1. (a) Searle, P. A.; Molinski, T. F. J. Am. Chem. Soc. 1995, 117, 8126-8131.
2. (b) Searle, P. A.; Molinski, T. F.; Brzezinski, L. J.; Leahy, J. W. J. Am. Chem. Soc. 1996, 118, 9422-9423.
3. (c) Molinski, T. F. Tetrahedron Lett. 1996, 37, 7879-7880.
4. Forsyth, C. J.; Ahmed, F.; Cink, R. D.; Lee, C. S. J. Am. Chem. Soc. 1998, 120, 5597-5598.
5. (a) Evans, D. A.; Fitch, D. M.; Smith, T. E.; Cee, V. J. J. Am. Chem. Soc. 2000, 122, 10033-10046.
6. (b) Evans, D. A.; Cee, V. J.; Smith, T. E.; Fitch, D. M.; Cho, P. S. Angew Chem., Int. Ed. 2000, 39, 2533-2536.
7. (c) Evans, D. A.; Fitch, D. M. Angew. Chem., Int. Ed. 2000, 39, 2536-2540.
8. (a) Smith, A. B., III; Minbiole, K. P.; Verhoest, P. R.; Schelhass, M. J. Am. Chem. Soc. 2001, 123, 10942-10953.
9. (b) Smith, A. B., III; Verhoest, P. R.; Minbiole, K. P.; Schelhaus, M. J. Am. Chem. Soc. 2001, 123, 4834-4836.
10. (a) Pattenden, G.; Gonzalez, M. A.; Little, P. B.; Millan, D. S.; Plowright, A. T.; Tornos, J. A.; Ye, T. Org. Biomol. Chem 2003, 1, 4173-4208.
11. (b) Gonzalez, M. A.; Pattenden, G. Angew. Chem., Int. Ed. 2003, 42, 1255-1258.
12. (a) Williams, D. R.; Kiryanov, A. A.; Emde, U.; Clark, M. P.; Berliner, M. A.; Reeves, J. T. PNAS 2004, 101, 12058-12063.
13. (b) Williams, D. R.; Kiryanov, A. A.; Emde, U.; Clark, M. P.; Berliner, M. A.; Reeves, J. T. Angew. Chem., Int. Ed. 2003, 42, 1258-1262.
14. For a review of the total syntheses, see: Haustedt, L. O.; Hartung, I. V.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. 2003, 42, 2711-2716.
15. For synthetic approaches to the bis-tetrahydropyran segment of the phorboxazoles, see: (a) Paterson, I.; Steven, A.; Luckhurst, C. A. Org. Biomol. Chem. 2004, 2, 3026-3038 and references therein.
16. (b) Lucas, B. S.; Luther, L. M.; Burke, S. D. Org. Lett. 2004, 6, 2965-2968.
17. (c) Zhang, D.-H.; Zhou, W.-S. Synlett 2003, 15, 1817-1821.
18. (d) Lucas, B. S.; Burke, S. D. Org. Lett. 2003, 5, 3915-3918.
19. (e) Greer, P. B.; Donaldson, W. A. Tetrahedron 2002, 58, 6009-6018 and references therein.
20. (a) Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271-7274.
21. (b) Rychnovsky, S. D.; Thomas, C. R. Org. Lett. 2000, 2, 1217-1219.
22. (c) Jaber, J. J.; Mitsui, K.; Rychnovsky, S. D. J. Org. Chem. 2001, 66, 4679-4686.
23. (d) Rychnovsky, S. D.; Marumoto, S.; Jaber, J. J. Org. Lett. 2001, 3, 3815-3818.
24. (e) Marumoto, S.; Jaber, J. J.; Vitale, J. P.; Rychnovsky, S. D. Org. Lett. 2002, 4, 3919-3922.
25. (f) Jasti, R.; Vitale, J. P.; Rychnovsky, S. D. J. Am. Chem. Soc. 2004, 126, 9904-9905.
26. (g) Dalgard, J. E.; Rychnovsky, S. D. Org. Lett. 2005, 7, 1589-1591.
27. For the preparation of α-acetoxy ethers, see: (a) Dahanukar, V. H.; Rychnovsky, S. D. J. Org. Chem. 1996, 61, 8317-8320.
28. (b) Kopecky, D. J.; Rychnovsky, S. D. J. Org. Chem. 2000, 65, 191-198.
29. (c) Kopecky, D. J.; Rychnovsky, S. D. Org. Synth. 2003, 80, 177-183.
30. (a) Alder, R. W.; Harvey, J. N.; Oakley, M. T. J. Am. Chem. Soc. 2002, 124, 4960-4961.
31. (b) Crosby, S. R.; Harding, J. R.; King, C. D.; Parker, G. D.; Willis, C. L. Org. Lett. 2002, 4, 577-580.
32. Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307-1315.
33. For the primary selective oxidation of 1,4- and 1,5-diols with IBX, see: (a) Corey, E. J.; Palani, A. Tetrahedron Lett. 1995, 38, 3485-3488.
34. (b) Corey, E. J.; Palani, A. Tetrahedron Lett. 1995, 36, 7945-7948.
35. Precedent for this stereochemical control element comes from the work of Kishi and Hosomi: (a) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978.
36. (b) Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383-2386.
37. White, J. D.; Kranemann, C. L.; Kuntyong, P. Org. Lett. 2001, 3, 4003-4006.
38. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467-8468.
39. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
40. Conditions for benzyl group cleavage were adapted from: Akiyama, T.; Hirofuji, H.; Ozaki, S. Tetrahedron Lett. 1991, 32, 1321-1324.
41. Vitale, J. P. Ph.D. Thesis, UC Irvine, 2002.
42. Jadhav, P. K.; Bhat, K. S.; Perumal, P. T.; Brown, H. C. J. Org. Chem. 1986, 51, 432-439.
43. It is noteworthy that treatment of α-acetoxy ether 11 under the same conditions provided solely fragmentation products 10 and 17.
44. This phenomenon is general and has been investigated. For a mechanistic rationale, see ref 9f.
45. Shimizu, T.; Hiranuma, S.; Nakata, T. Tetrahedron Lett. 1996, 37, 6145-6148.
46. Conditions for the cyclization were adapted from: Barry, C. S. J.; Crosby, S. R.; Harding, J. R.; Hughes, R. A.; King, C. D.; Parker, G. D.; Willis, C. L. Org. Lett. 2003, 5, 2429-2432.
47. The second route to 13 using the TFA cyclization was the most concise and proceeded in 13 steps from epoxide 3. The overall yield for this route, including recycling of the minor epimer of 23, was 13.2%.