Iododesilylation of TIPS-, TBDPS-, and TBS-substituted alkenes in connection with the synthesis of amphidinolides B/D

Organic Letters

Volumn 13, Issue 18, 2011, Pages 4934-4937

  Sidera, Mireia ^a   Costa, Anna M ^a   Vilarrasa, Jaume ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMPHIDINOLIDE D; FUSED HETEROCYCLIC RINGS;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKENES; BICYCLO COMPOUNDS, HETEROCYCLIC; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 80052696874     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2020187     Document Type: Article

References (36)

1. Sidera, M. PhD Thesis, Universitat de Barcelona (2007-2011).
2. Kobayashi, J. J. Antibiot. 2008, 61, 271
3. Kobayashi, J.; Kubota, T. J. Nat. Prod. 2007, 70, 451
4. Lu, L.; Zhang, W.; Carter, R. G. J. Am. Chem. Soc. 2008, 130, 7253 (B1 and B2, allyl silane addition to a methyl ketone, C14-C15), and references therein
5. Fürstner, A.; Bouchez, L. C.; Morency, L.; Funel, J.-A.; Liepins, V.; Poree, F.-H.; Gilmour, R.; Laurich, D.; Beaufils, F.; Tamiya, M. Chem.-Eur. J. 2009, 15, 3983 (B1, B4, G1, H1, and H2, Stille coupling).
6. Fürstner, A.; Bouchez, L. C.; Funel, J.-A.; Liepins, V.; Poree, F.-H.; Gilmour, R.; Beaufils, F.; Laurich, D.; Tamiya, M. Angew. Chem., Int. Ed. 2007, 46, 9265
7. Petri, A. F.; Schneekloth, J. S.; Mandal, A. K.; Crews, C. M. Org. Lett. 2007, 9, 3001
8. Formentin, P.; Murga, J.; Carda, M.; Marco, J. A. Tetrahedron: Asymmetry 2006, 17, 2938
9. Gopalarathnam, A.; Nelson, S. G. Org. Lett. 2006, 8, 7
10. Fürstner, A. Isr. J. Chem. 2011, 51, 329
11. Soderquist, J. A.; Colberg, J. C.; Valle, L. D. J. Am. Chem. Soc. 1989, 111, 4873
12. There is only one related example, the desilylation of 2-TIPS-2-cyclopentenone with ICl. See: Davie, C. P.; Danheiser, R. L. Angew. Chem., Int. Ed. 2005, 44, 5867
13. Ilardi, E. A.; Stivala, C. E.; Zakarian, A. Org. Lett. 2008, 10, 1727
14. In our group, this procedure had been applied to the cleavage of a C-TMS bond arising from a Si-tethered RCM: Rodríguez-Escrich, C.; Urpí, F.; Vilarrasa, J. Org. Lett. 2008, 10, 5191
15. Xie, Q.; Denton, R. W.; Parker, K. A. Org. Lett. 2008, 10, 5345
16. Martin, D. B. C.; Vanderwal, C. D. J. Am. Chem. Soc. 2009, 131, 3472
17. Herrmann, A. T.; Martinez, S. R.; Zakarian, A. Org. Lett. 2011, 13, 3636
18. Parker, K. A.; Denton, R. W. Tetrahedron Lett. 2011, 52, 2115
19. Pawluc, P.; Franczyk, A.; Walkowiak, J.; Hreczycho, G.; Kubicki, M.; Marciniec, B. Org. Lett. 2011, 13, 1976
20. Denmark, S. E.; Muhuhi, J. M. J. Am. Chem. Soc. 2010, 132, 11768
21. Pawluc, P.; Madalska, M.; Hreczycho, G.; Marciniec, B. Synthesis 2008, 3687
22. 4. See: Djerassi, C.; Lenk, C. T. J. Am. Chem. Soc. 1953, 75, 3493
23. Dolenc, D. Synlett 2000, 544
24. Rai, A. Synlett 2008, 784 and references cited therein. NISac has not been used in iododesilylations
25. Orazi, O. O.; Corral, R. A.; Bertorello, H. E. J. Org. Chem. 1965, 30, 1101
26. Creighton, J. A.; Haque, I.; Wood, J. L. Chem. Commun. 1966, 229
27. Barluenga, J.; González, J. M.; Campos, P. J.; Asensio, G. Angew. Chem. 1985, 97, 341
28. Barluenga, J.; Alvarez-García, L. J.; González, J. M. Tetrahedron Lett. 1995, 36, 2153
29. Barluenga, J.; Llorente, I.; Alvarez-García, L. J.; González, J. M.; Campos, P. J.; Díaz, M. R.; García-Granda, S. J. Am. Chem. Soc. 1997, 119, 6933
30. Also see ref 8h and references cited therein. Miyaura, N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; de Meijere, A., Eds.; Wiley-VCH: New York, 2004; Chapter 2.
31. Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633
32. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457
33. Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I.; Ed.; Wiley-VCH: New York, 2000; Chapter 6A.
34. 2)Br. See: Evans, D. A.; Bender, S. L.; Morris, J. J. Am. Chem. Soc. 1988, 8, 2506
35. Negishi, E..; Swanson, D. R.; Rousset, C. J. J. Org. Chem. 1990, 55, 5406
36. Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404