Synthesis of (+)-didemniserinolipid B via ketalization/ring-closing metathesis

Organic Letters

Volumn 9, Issue 26, 2007, Pages 5357-5359

  Marvin, Christopher C ^a   Voight, Eric A ^a   Burke, Steven D ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIDEMNISERINOLIPID B; ETHER DERIVATIVE; PROPANEDIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

CYCLIZATION; ETHERS; PROPYLENE GLYCOLS;

EID: 38349101397     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702454m     Document Type: Article

References (39)

1. González, N.; Rodriguez, J.; Jiménez, C. J. Org. Chem. 1999, 64, 5705.
2. Mitchell, S. S.; Rhodes, D.; Bushman, F. D.; Faulkner, D. J. Org. Lett. 2000, 2, 1605.
3. Kiyota, H.; Dixon, D. J.; Luscombe, C. K.; Hettstedt, S.; Ley, S. V. Org. Lett. 2002, 4, 3223.
4. (a) Marvin, C. C.; Clemens, A. J. L.; Burke, S. D. Org. Lett. 2007, 9, 5353.
5. (b) Voight, E. A.; Seradj, H.; Roethle, P. A.; Burke, S. D. Org. Lett. 2004, 6, 4045.
6. (c) Voight, E. A.; Rein, C.; Burke, S. D. J. Org. Chem. 2002, 67, 8489.
7. (d) Keller, V. A.; Martinelli, J. R.; Strieter, E. R.; Burke, S. D. Org. Lett. 2002, 4, 467.
8. (e) Voight, E. A.; Rein, C.; Burke, S. D. Tetrahedron Lett. 2001, 42, 8747.
9. (f) Burke, S. D.; Voight, E. A. Org. Lett. 2001, 3, 237.
10. (g) Burke, S. D.; Müller, N.; Beaudry, C. M. Org. Lett. 1999, 1, 1827.
11. For recent reviews, see: (a) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490.
12. (b) Grubbs, R. H. Tetrahedron 2004, 60, 7117.
13. (c) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199.
14. (d) Vernall, A. J.; Abell, A. D. Aldrichimica Acta 2003, 36, 93.
15. (e) Connon, S. J.; Blechert. S. Angew. Chem., Int. Ed. 2003, 42, 1900.
16. (f) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
17. (g) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
18. For other selective epoxidations of endocyclic alkenes, see: (a) Azzari, E.; Faggi, C.; Gelsomini, N.; Taddei, M. Tetrahedron Lett. 1989, 30, 6067.
19. (b) Tchilibon, S.; Mechoulam, R. Org. Lett. 2000, 2, 3301.
20. (c) Hanus, L. O.; Tchilibon, S.; Ponde, D. E.; Breuer, A.; Fride, E.; Mechoulam, R. Org. Biomol. Chem. 2005, 3, 1116.
21. Fürst, A.; Plattner, P. A. Helv. Chim. Acta 1949, 32, 275.
22. (a) Williamson, W. Liebigs Ann. Chem. 1851, 77, 37.
23. (b) Williamson, W. J. Chem. Soc. 1852, 106, 229.
24. (a) Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361.
25. (b) Dondoni, A.; Perrone, D. Org. Synth. 2004, 10, 320.
26. Burke, S. D.; Sametz, G. M. Org. Lett. 1999, 1, 71.
27. 16-Hexadecanolide 7 was opened with lithiated dimethyl methylphosphonate to generate a β-ketophosphonate and immediately subjected to Horner-Wadsworth-Emmons olefination with phenylacetaldehyde to yield β,γ-unsaturated ketone 8. The presence of the phenyl ring promoted isomerization of the double bond from the α,β- to the β,γ-position, which was essential for the required RCM. Standard mesylation conditions provided 5.
28. Marshall, J. A.; Sabatini, J. J. Org. Lett. 2005, 7, 4819.
29. Krauss, I. J.; Mandal, M.; Danishefsky. S. J. Angew. Chem., Int. Ed. 2007, 46, 5576.
30. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
31. (a) Pasto, D. J.; Taylor, R. T. Org. React. 1991, 40, 91.
32. (b) Wiberg, N.; Fischer, G.; Bachhuber, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 385.
33. (a) Reich, H. J.; Wollowitz, S. Org. React. 1993, 44, 1.
34. (b) Reich, H. J. Acc. Chem. Res. 1979, 12, 22.
35. (c) Reich, H. J.; Reich, I. L.; Renga, J. M. J. Am. Chem. Soc 1973, 95, 5813.
36. (d) Sharpless, K. B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137.
37. Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
38. Ley and co-workers reported a two-step yield of 49% for this sequence. See ref 3.
39. See the Supporting Information.