Toward the synthesis of spirastrellolide B: A synthesis of the C1-C23 subunit

Organic Letters

Volumn 10, Issue 6, 2008, Pages 1083-1086

  Keaton, Katie A ^a   Phillips, Andrew J ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MACROLIDE; SPIRASTRELLOLIDE B; SPIRO COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

MACROLIDES; MOLECULAR STRUCTURE; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 45549087251     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702955m     Document Type: Article

References (28)

1. Williams, D. E.; Roberge, M.; Van Soest, R.; Andersen, R. J. J. Am. Chem. Soc. 2003, 125, 5296.
2. Williams, D. E.; Lapawa, M.; Feng, X.; Tarling, T.; Roberge, M.; Andersen, R. J. Org. Lett. 2004, 6, 2607.
3. Warabi, K.; Williams, D. E.; Patrick, B. O.; Roberge, M.; Andersen, R. J. J. Am. Chem. Soc. 2007, 129, 508.
4. Williams, D. E.; Keyzers, R. A.; Warabi, K.; Desjardine, K.; Riffell, J. L.; Roberge, M.; Andersen, R. J. J. Org. Chem. 2007, 72, 9842.
5. Liu, J.; Hsung, R. P. Org. Lett. 2005, 7, 2273.
6. Liu, J.; Yang, J. H.; Ko, C.; Hsung, R. P. Tetrahedron Lett. 2006, 47, 6121.
7. Ghosh, S. K.; Ko, C.; Liu, J.; Wang, J.; Hsung, R. P. Tetrahedron 2006, 62, 10485.
8. (a) Paterson, I.; Anderson, E. A.; Dalby, S. M.; Loiseleur, O. Org. Lett. 2005, 7, 4125.
9. (b) Paterson, I.; Anderson, E. A.; Dalby, S. M.; Loiseleur, O. Org. Lett. 2005, 7, 4121.
10. (c) Paterson, I.; Anderson, E. A.; Dalby, S. M.; Lim, J. H.; Maltas, P.; Moessner, C. Chem. Commun. 2006, 4186.
11. (d) Paterson, I.; Anderson, E. A.; Dalby, S. M.; Genovino, J.; Lim, J. H.; Moessner, C. Chem. Commun. 2007, 1852.
12. (a) Furstner, A.; Fenster, M. D. B.; Fasching, B.; Godbout, C.; Radkowski, K. Angew. Chem., Int. Ed. 2006, 45, 5506.
13. (b) Furstner, A.; Fenster, M. D. B.; Fasching, B.; Godbout, C.; Radkowski, K. Angew. Chem., Int. Ed. 2006, 45, 5510.
14. (c) Furstner, A.; Fasching, B.; O'Neil, G. W.; Fenster, M. D. B.; Godbout, C.; Ceccon, J. Chem. Commun. 2007, 3045.
15. Pan, Y.; De Brabander, J. K. Synlett 2006, 853.
16. (a) Wang, C.; Forsyth, C. J. Org. Lett. 2006, 8, 2997.
17. (b) Wang, C.; Forsyth, C. J. Heterocycles 2007, 72, 621.
18. Smith, A. B., III; Kim, D.-S. Org. Lett. 2007, 9, 3311.
19. Keaton, K. A.; Phillips, A. J. Org. Lett. 2007, 9, 2717.
20. Schaus, S. E : Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. J. Am. Chem. Soc. 2002, 124, 1307.
21. Tamura M.; Kochi J. Synthesis 1971, 303.
22. For pioneering studies on the opening of cyclopropanols with Fe-(III) species to give β-chloroketones, see: (a) Schaafsma, S. E.; Steinberg, H.; De Boer, Th. J. Recl. Trav. Chim. Pays-Bas 1966, 85, 73.
23. (b) Schaafsma, S. E.; Steinberg, H.; De Boer, Th. J. Recl. Trav. Chim. Pays-Bas 1966, 85, 70.
24. Booker-Milburn has also observed β-chloroesters as products in the opening of cyclopropenone acetals with Fe(III): Booker-Milburn, K. I.; Cox, B.; Mansley, T. E. Chem. Commun. 1996, 2577.
25. Jiang, B.; Chen, Z.; Xiong, W. Chem. Commun. 2002, 1524.
26. (a) Chan. K.; Cohen, N.; DeNoble, J. P.; Specian, A. C.; Saucy, G. J. Org. Chem. 1976, 41, 3497.
27. (b) Denmark, S. E.; Jones, T. K. J. Org. Chem. 1982, 47, 4595.
28. For the initial report describing these conditions for Kulinkovich, cyclopropanation, see: Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 4198.