Total synthesis of (-)-dictyostatin

Journal of the American Chemical Society

Volumn 128, Issue 16, 2006, Pages 5340-5341

  O'Neil, Gregory W ^a   Phillips, Andrew J ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DICTYOSTATIN; MACROLIDE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

MACROLIDES; OXIDATION-REDUCTION;

EID: 33646453676     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0609708     Document Type: Article

References (24)

1. Isbrucker, R. A.; Cummins, J.; Pomponi, S. A.; Longley, R. E.; Wright, A. E. Biochem. Pharmacol. 2003, 66, 75.
2. (a) Pettit, G. R.; Cichacz, Z. A.; Gao, F.; Boyd, M. R.; Schmidt, J. M. J. Chem. Soc., Chem. Commun. 1994, 1111.
3. (b) Pettit, G. R.; Cichacz, Z. A. WO 5430053, 1995; Chem. Abstr. 1995, 733500.
4. Stereochemical assignment: Paterson, I.; Britton, R.; Delgado, O.; Wright, A. E. Chem. Commun. 2004, 632.
5. Paterson, I.; Britton, R.; Delgado, O.; Meyer, A.; Poullennec, K. G. Angew. Chem., Int. Ed. 2004, 43, 4629.
6. Shin, Y.; Fournier, J.-H.; Fukui, Y.; Bruckner, A. M.; Curran, D. P. Angew. Chem., Int. Ed. 2004, 43, 4634.
7. O'Neil, G. W.; Phillips, A. J. Tetrahedron Lett. 2004, 45, 4253.
8. Crimmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. J. Org. Chem. 2001, 66, 894.
9. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
10. Synthesized by a route analogous to that described in ref 6.
11. For the synthesis of acid 3, see the Supporting Information.
12. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
13. Curran has recently described the cyclization of substrates related to 15 by RCM. See: Kangani, C. O.; Bruckner, A. M.; Curran, D. P. Org. Lett. 2005, 7, 379.
14. (a) Sinisterra, J. V.; Mouloungui, Z.; Delmas, M.; Gaset, A. Synthesis 1985, 1097.
15. (b) Paterson, I.; Yeung, K.-S.; Smaill, J. B. Synlett 1993, 774.
16. Mahoney, W. S.; Brestensky, D. M.; Stryker, J. M. J. Am. Chem. Soc. 1988, 110, 291.
17. Oishi, T.; Nakata, T. Acc. Chem. Res. 1984, 17, 338.
18. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
19. For other recent examples of macrolide synthesis by Z-selective intramolecular Still-Gennari-modified Horner-Wadsworth-Emmons reaction, see: (a) Forsyth, C. J.; Ahmed, F.; Cink, R. D.; Lee, C. S. J. Am. Chem. Soc. 1998, 120, 5597.
20. (b) Smith, A. B.; Verhoest, P. R.; Minbiole, K. P.; Schelhaas, M. J. Am. Chem. Soc. 2001, 123, 10942.
21. (c) Williams, D. R.; Kiryanov, A. A.; Emde, U.; Clark, M. P.; Berliner, M. A.; Reeves, J. T. Angew. Chem., Int. Ed. 2003, 42, 1258.
22. (d) González, M. A.; Pattenden, G. Angew. Chem., Int. Ed. 2003, 42, 1255.
23. (e) Ghosh, A. K.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027.
24. + 533.3836, found 533.3831. For a comparison of NMR data, see the Supporting Information.