Intramolecular alkynylogous mukaiyama aldol reaction starting from bicyclic alkanones tethered to alkynyl esters: Formal total synthesis Of (±)-Hamigeran B

Chemistry - A European Journal

Volumn 15, Issue 17, 2009, Pages 4394-4401

  Miesch, Laurence ^a   Welsch, Tania ^a   Rietsch, Vincent ^a   Miesch, Michel ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Aldol reaction; Allenes; Cascade reactions; Sleteoselectivity; Total synthesis

Indexed keywords

ALDOL REACTION; ALLENES; CASCADE REACTIONS; SLETEOSELECTIVITY; TOTAL SYNTHESIS;

AVIATION; ESTERIFICATION; SILANES;

ESTERS;

3-HYDROXYBUTANAL; ALDEHYDE; ALDOL; ALKADIENE; ALLENE; ESTER; HAMIGERAN B; NAPHTHOQUINONE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; SPONGE (PORIFERA); STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALDEHYDES; ALKADIENES; ANIMALS; CRYSTALLOGRAPHY, X-RAY; ESTERS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NAPHTHOQUINONES; PORIFERA; STEREOISOMERISM;

EID: 65349184463     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802309     Document Type: Article

References (36)

1. K. C. Nicolaou, D. J. Edmons, G. Bulger, Angew. Chem. 2006, 118, 7292-7344;
2. Angew. Chem. Int. Ed. 2006, 45, 7134-7186.
3. A. J. Mota, A. Klein, F. Wendling, A. Dedieu, M. Miesch, Eur. J. Org. Chem. 2005, 4346-4358.
4. Preliminary report: L. Miesch, V. Rietsch, T. Welsch, M. Miesch, Tetrahedron Lett. 2008, 49, 5053-5055.
5. K. D. Wellington, R. C. Cambrie, P. S. Rutledge, P. R. Berquist, J. Nat. Prod. 2000, 63, 79-85.
6. W. H. Gerwick, W. Fenical, M. U. S. Sultanbawa, J. Org. Chem. 1981,46,2233-2241.
7. a) J. S. Liu, H. X. Zhou, L. Li, Phytochemistry 1992, 31, 1379-1392;
8. b) Y. C. Shen, C. C. Liaw, Y. B. Cheng, A. F. Ahmed, M. C. Lai, S. S. Liou, T. S. Wu, Y. H. Kuo, Y. C. Lin, J. Afar. Prod. 2006, 69, 963-966.
9. a) M. Toyota, A. llangovan, R. Okamoto, T. Masaki, M. Arakawa, M. Ihara, Org. Lett. 2002, 4, 4293-4296;
10. b) P. K. Koech, M. J. Kri-sche, Org. Lett. 2004, 6, 691-694;
11. c) K. Agapiou, D. F. Cauble, M. J. Krische, J. Am. Chem. Soc. 2004, 126, 4528-4529.
12. a) R. E. Ireland, D. A. Evans, P. Lologer, J. Bordner, R. H. Stanford, R. E. Dickerson, J. Org. Chem. 1969, 34, 3729-3739;
13. b) R. Jaffe, T. Elisme, A. C. Cabrera, Org. Geochem. 1996, 25, 9-17.
14. D. L. J. Clive, J. Wang, J. Org. Chem. 2004, 69, 2773-2784.
15. Microwave activation is an essential requirement for an effective al-kylation reaction. Without activation, the yield dropped (50% instead of 70%) and the reaction took longer (24 h instead of 3 min). The microwave device used was: START SYSTEM from: MILESTONE S.r.l. Via Fatebenefratelli, 1/524010 Sorisole (BG)-Italy. The reaction was run in an open vessel in DMF (power: 400 W) for 10s. For a leading reference concerning microwave activation, see: L. Perreux, A. Loupy in Microwaves in Organic Synthesis Vol. 1 (Ed: A. Loupy), Wiley-VCH, Weinheim, 2006, pp. 134-218.
16. CCDC-705050 contains the supplementary crystal lographic data for compound 11. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data-request/cif
17. F. Wendling, M. Miesch, Org. Lett. 2001, 3, 2689-2691.
18. CCDC-656100 contains the supplementary crystallographic data for compound 14. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data-request/cif
19. CCDC-705048 contains the supplementary crystallographic data for compound 19. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data-request/cif
20. M. Ihara, Arkivoc 2006, 416-438, and references therein.
21. S. D. Lepore, Y. He, P. Damisse, J. Org. Chem. 2004, 69, 9171-9175.
22. A. F. Lechevallier, M. Pellet, J. M. Conia, Synthesis 1978, 63-65.
23. For intermolecular version, see: a) B. Xu, G. B. Hammond, Angew. Chem. 2008, 120, 701-704;
24. Angew. Chem. Int. Ed. 2008, 47, 689-692;
25. b) L. P. Liu, B. Xu, G. B. Hammond, Org. Lett. 2008, 10, 3887-3890;
26. c) W Wang, B. Xu, G. B. Hammond, Org. Lett. 2008, 10, 3713-3716.
27. a) K. C. Nicolaou, D. Gray, J. Tae, Angew. Chem. 2001, 113, 3787-3790;
28. Angew. Chem. Int. Ed. 2001, 40, 3675-3678;
29. b) K. C. Nicolaou, D. Gray, J. Tae, J. Am. Chem. Soc. 2004, 126, 613-627;
30. c) B. M. Trost, C. Pissot-Soldermann, I. Chen, G. M. Schroeder, J. Am. Chem. Soc. 2004, 126, 4480-4481;
31. d) B. M. Trost, C. Pissot-Soldermann, I. Chen, Chem. Eur. J. 2005, 11, 951-959;
32. e) D. L. J. Clive, J. Wang, Angew. Chem. 2003, 115, 3528-3531;
33. Angew. Chem. Int. Ed. 2003, 42, 3406-3409;
34. f) D. L. J. Clive, J. Wang, J. Org. Chem. 2004, 69, 2773-2784;
35. g) D. F. Taber, W. Tian, J. Org. Chem. 2008, 73, 7560-7564;
36. h) for an excellent review see: D. L. J. Clive. J. Wang, Org. Prep. 2005,57, 1-35.