Synthesis of (-)-lapatin B

Tetrahedron Letters

Volumn 48, Issue 35, 2007, Pages 6214-6216

  Walker, Steven J ^a   Hart, David J ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALANTRYPINONE; GLYANTRYPINE; INDOLE; LAPATIN B; N,N DIACETYLGLYANTRYPINE; OXINDOLE; QUINAZOLINE DERIVATIVE; TRYPTOPHAN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; DRUG TRANSFORMATION; OXIDATION;

EID: 34547517527     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.089     Document Type: Article

References (26)

1. Larsen T.O., Petersen B.O., Duus J.Ø., Sørensen D., Frisvad J.C., and Hansen M.E. J. Nat. Prod. 68 (2005) 871-874
2. Larsen T.O., Frydenvang K., Frisvad J.C., and Christophersen C. J. Nat. Prod. 61 (1998) 1154-1157
3. For other members of this family of alkaloids, see:. Barrow C.J., and Sun H.H. J. Nat. Prod. 57 (1994) 471-476 (spiroquinazoline)
4. Ariza M.R., Larsen T.O., Petersen B.O., Duus J.Ø., Christophersen C., and Barrero A.F. J. Nat. Prod. 64 (2001) 1590-1592 (serantrypinone)
5. Kuriyama T., Kakemoto E., Takahashi N., Imamura K., Oyama K., Suzuki E., Harimaya K., Yaguchi T., and Ozoe Y. J. Agric. Food Chem. 52 (2004) 3884-3887 (alantrypinone and serantrypinone)
6. Proença Barros F.A., and Rodrigues-Filho E. Biochem. Syst. Ecol. 33 (2005) 257-268 (alanditrypinone, alantryphenone and alantryleunone)
7. For a relevant review see:. Mhaske S.B., and Argade N.P. Tetrahedron 62 (2006) 9787-9826
8. Hart D.J., and Magomedov N.A. Tetrahedron Lett. 40 (1999) 5429-5432
9. Hart D.J., and Magomedov N.A. J. Am. Chem. Soc. 123 (2001) 5892-5899
10. For a synthesis of rac-alantrypinone see:. Chen Z., Fan J., and Kende A.S. J. Org. Chem. 69 (2004) 79-85
11. A total synthesis of (rac)-lapatin B has recently been described:. Leca D., Gaggini F., Cassayre J., Loiseleur O., Pieniazek S.N., Luft J.A.R., and Houk K.N. J. Org. Chem. 72 (2007) 4284-4287
12. 8-11 the absolute configuration of the natural product remains unknown
13. Liu J.-F., Ye P., Zhang B., Bi G., Sargent K., Yu L., Yohannes D., and Baldino C.M. J. Org. Chem. 70 (2005) 6339-6345
14. Cledera P., Avendaño C., and Menéndez J.C. J. Org. Chem. 65 (2000) 1743-1749
15. Hernández F., Lumetzberger A., Avendaño C., and Söllhuber M. Synlett (2001) 1387-1390
16. Wang H., and Ganesan A. J. Org. Chem. 65 (2000) 1022-1030
17. For other work describing this type of rearrangement see:. He F., and Snider B.B. J. Org. Chem. 64 (1999) 1397-1399
18. Mazurkiewicz R. Monatsh. Chem. 120 (1989) 973-980
19. Sánchez J.D., Ramos M.T., and Avendaño C. J. Org. Chem. 66 (2001) 5731-5735
20. Martín-Santamaría S., Espada M., and Avendaño C. Tetrahedron 55 (1999) 1755-1762
21. Koser G.F., Relenyi A.G., Kalos A.N., Rebrovic L., and Wettach R.H. J. Org. Chem. 47 (1982) 2487-2489
22. A number of oxindole-to-indole reaction sequences have been reported. We followed the protocols described by Pellegrini [Pellegrini, C.; Strässler, C.; Weber, M.; Borschberg, H.-J. Tetrahedron: Asymmetry 1994, 5, 1979-1992; Stahl, R.; Borschberg, H.-J.; Acklin, P. Helv. Chim. Acta 1996, 79, 1361-1378] and did not examine other protocols.
23. 4
24. 4
25. 6
26. Chiral HPLC analysis (Chiracel OJ column eluted with hexane/i-PrOH, 4:1) of synthetic 1 indicated the presence of only one enantiomer. (rac)-Lapatin, prepared from (rac)-8 (see text) was used to develop a baseline separation of 1 and (ent)-1.