Use of a tandem Prins/Friedel-Crafts reaction in the construction of the indeno-tetrahydropyridine core of the haouamine alkaloids: Formal synthesis of (-)-haouamine A

Organic Letters

Volumn 13, Issue 10, 2011, Pages 2614-2617

  Fenster, Erik ^a   Fehl, Charlie ^a   Aubé, Jeffrey ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; FUSED HETEROCYCLIC RINGS; HAOUAMINE A;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; UROCHORDATA;

ALKALOIDS; ANIMALS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MOLECULAR STRUCTURE; STEREOISOMERISM; UROCHORDATA;

EID: 79956147556     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200725m     Document Type: Article

References (23)

1. Garrido, L.; Zubia, E.; Ortega, M. J.; Salvá, J. J. Org. Chem. 2003, 68, 293-299
2. For previous total syntheses of haouamine A, see: Baran, P. S.; Burns, N. Z. J. Am. Chem. Soc. 2006, 128, 3908-3909
3. Burns, N. Z.; Baran, P. S. Angew. Chem., Int. Ed. 2008, 47, 205-208
4. Burns, N. Z.; Krylova, I. N.; Hannoush, R. N.; Baran, P. S. J. Am. Chem. Soc. 2009, 131, 9172-9173
5. For previous formal syntheses of haouamine A, see: Jeong, J. H.; Weinreb, S. M. Org. Lett. 2006, 8, 2309-2312
6. Fürstner, A.; Ackerstaff, J. Chem. Commun. 2008, 2870-2872
7. Taniguchi, T.; Zaimoku, H.; Ishibashi, H. J. Org. Chem. 2009, 74, 2624-2626
8. For previous approaches to the haouamines, see: Smith, N. D.; Hayashida, J.; Rawal, V. H. Org. Lett. 2005, 7, 4309-4312
9. Grundl, M. A.; Trauner, D. Org. Lett. 2006, 8, 23-25
10. Wipf, P.; Furegati, M. Org. Lett. 2006, 8, 1901-1904
11. Tanaka, T.; Inui, H.; Kida, H.; Kodama, T.; Okamoto, T.; Takeshima, A.; Tachi, Y.; Morimoto, Y. Chem. Commun. 2011, 47, 2949-2951
12. Yang, X.-F.; Wang, M.; Zhang, Y.; Li, C.-J. Synlett 2005, 1912-1916
13. Tian, X.; Jaber, J. J.; Rychnovsky, S. D. J. Org. Chem. 2006, 71, 3176-3183
14. Basavaiah, D.; Reddy, K. R. Org. Lett. 2007, 9, 57-60
15. Reddy, U. C.; Bondalapati, S.; Saikia, A. K. J. Org. Chem. 2009, 74, 2605-2608
16. Reddy, U. C.; Saikia, A. K. Synlett 2010, 1027-1032
17. We suspect that the dehydration leading to 9 occurs competitively with the desired Friedel-Crafts reaction. In a polar aprotic solvent such as nitromethane, the intermediate Prins carbocation remains longer lived so as to allow sufficient time for the Friedel-Crafts arene to react directly.
18. Serine iodide 12 is prepared in three steps from serine (methyl ester formation, Boc protection, iodination) in 61% overall yield according to the procedure of Rudd, M. T.; Trost, B. M. Org. Lett. 2003, 5, 4599-4602
19. Rilatt, I.; Caggiano, L.; Jackson, R. F. W. Synlett 2005, 2701-2719
20. Oswald, C. L.; Carrillo-Márquez, T. S.; Caggiano, L.; Jackson, R. F. W. Tetrahedron 2008, 64, 681-687
21. Ross, A. J.; Lang, H. L.; Jackson, R. F. W. J. Org. Chem. 2010, 75, 245-248
22. Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, H., U.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461-5464
23. Various olefination methods involving Wittig and Tebbe reagents failed to produce substantial amounts of the product. The Peterson olefination method was successful only in the cases where the intermediate silane was treated in acid conditions (base conditions were found to be incompatible with the Boc protecting group).