Formal Alder-ene reaction of a bicyclo[1.1.0]butane in the synthesis of the tricyclic quaternary ammonium core of daphniglaucins

Tetrahedron Letters

Volumn 49, Issue 41, 2008, Pages 5986-5989

  Ueda, Masafumi ^a   Walczak, Maciej A A ^a   Wipf, Peter ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; BICYCLO[1.1.0]BUTANE; BUTANE; DAPHNIGLAUCIN; NITROGEN; QUATERNARY AMMONIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

ALNUS;

EID: 50049105287     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.07.179     Document Type: Article

References (32)

1. For recent examples, see:. Hung T.M., Ngoc T.M., Youn U.J., Min B.S., Na M.K., Thuong P.T., and Bae K.H. Biol. Pharm. Bull. 31 (2008) 159
2. Wu Y.-R., Ma Y.-B., Zhao Y.-X., Yao S.-Y., Zhou J., Zhou Y., and Chen J.-J. Planta. Med. 73 (2007) 787
3. Bai L.-P., Zhao Z.-Z., Cai Z., and Jiang Z.-H. Bioorg. Med. Chem. 14 (2006) 5439
4. Jayasuriya H., Herath K.B., Ondeyka J.G., Polishook J.D., Bills G.F., Dombrowski A.W., Springer M.S., Siciliano S., Malkowitz L., Sanchez M., Guan Z., Tiwari S., Stevenson D.W., Borris R.P., and Singh S.B. J. Nat. Prod. 67 (2004) 1036
5. For reviews, see:. Hashimoto T., and Maruoka K. Chem. Rev. 107 (2007) 5656
6. Maruoka K., Ooi T., and Kano T. Chem. Commun. (2007) 1487
7. O'Donnell M. Acc. Chem. Res. 37 (2004) 506
8. Kubota T., Sunaura T., Morita H., Mikami Y., Hoshino T., Obara Y., Nakahata N., and Kobayashi J. Heterocycles 69 (2006) 469
9. Ishiyama H., Matsumoto M., Sekiguchi M., Shigemori H., Ohsaki A., and Kobayashi J. Heterocycles 66 (2005) 651
10. Kobayashi J., Takatsu H., Shen Y.-C., and Morita H. Org. Lett. 5 (2003) 1733
11. Takatsu H., Morita H., Shen Y.-C., and Kobayashi J. Tetrahedron 60 (2004) 6279
12. Morita H., Takatsu H., Shen Y.-C., and Kobayashi J. Tetrahedron Lett. 45 (2004) 901
13. Kobayashi J., Sekiguchi M., Shimamoto S., Shigemori H., Ishiyama H., and Ohsaki A. J. Org. Chem. 67 (2002) 6449
14. Penelle J., Tits M., Christen P., Molgo J., Brandt V., Frédérich M., and Angenot L. Phytochemistry 53 (2000) 1057
15. Penelle J., Tits M., Christen P., Brandt V., Frédérich M., and Angenot L. J. Nat. Prod. 62 (1999) 898
16. For the use of an 1-(arylsulfonyl)bicyclobutane in the synthesis of two isoprenoids, see:. Gaoni Y., and Tomazic A. J. Org. Chem. 50 (1985) 2948
17. Wipf P., Stephenson C.R.J., and Okumura K. J. Am. Chem. Soc. 125 (2003) 14694
18. Wipf P., and Walczak M.A.A. Angew. Chem., Int. Ed. 45 (2006) 4172
19. Walczak M.A.A., and Wipf P. J. Am. Chem. Soc. 130 (2008) 6924 and references cited therein
20. Angehrn P., Buchmann S., Funk C., Goetschi E., Gmuender H., Hebeisen P., Kostrewa D., Link H., Luebbers T., Masciadri R., Nielsen J., Reindl P., Ricklin F., Schmitt-Hoffmann A., and Theil F. J. Med. Chem. 47 (2004) 1487
21. Côté A., Boezio A.A., and Charette A.B. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5405
22. Weber J., Haslinger U., and Brinker U.H. J. Org. Chem. 64 (1999) 6085
23. DeBoef B., Counts W.R., and Gilbertson S.R. J. Org. Chem. 72 (2007) 799
24. 2 (AcOEt) to give the major isomer 15 (942 mg, 52%).
25. 3PNa (M+Na) 688.2957, found 688.2964.
26. For reactions of bicyclo[1.1.0]butanes with benzyne that afforded a mixture of ene and other cycloaddition products, see:. Pomerantz M., Gruber G.W., and Wilke R.N. J. Am. Chem. Soc. 90 (1968) 5040
27. Pomerantz M., Wilke R.N., Gruber G.W., and Roy U. J. Am. Chem. Soc. 94 (1972) 2752
28. Gassman P.G., and Richmond G.D. J. Am. Chem. Soc. 90 (1968) 5637
29. Gassman P.G., and Richmond G.D. J. Am. Chem. Soc. 92 (1970) 2090
30. Yu W., Mei Y., Kang Y., Hua Z., and Jin Z. Org. Lett. 6 (2004) 3217
31. - counterions.
32. 2 (M-Cl or M-OMs) 316.2277, found 316.2265.