The application of vinylogous iminium salt derivatives to the synthesis of Ningalin B hexamethyl ether

Tetrahedron

Volumn 59, Issue 2, 2003, Pages 207-215

  Gupton, John T ^a   Clough, Stuart C ^a   Miller, Robert B ^a   Lukens, John R ^a   Henry, Charlotte A ^a   Kanters, René P F ^a   Sikorski, James A ^b  

^a UNIVERSITY OF RICHMOND   (United States)

^b AtheroGenics Inc   (United States)

Author keywords

chloroenal; Chloropropeniminium salt; Ningalin B; Trisubstituted pyrrole

Indexed keywords

IMINE; INORGANIC SALT; LAMELLARIN G TRIMETHYL ETHER; LAMELLARIN O; LUKIANOL A; NATURAL PRODUCT; NINGALIN B; NINGALIN B HEXAMETHYL ETHER; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; HYDROLYSIS; MULTIDRUG RESISTANCE; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0037421134     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01475-8     Document Type: Article

References (25)

1. Kang H., Fenical W. J. Org. Chem. 62:1997;3254.
2. Boger D., Soenen D., Boyce C., Hedrick M., Jin Q. J. Org. Chem. 65:2000;2479.
3. Boger D., Boyce C., Labroli M., Sehon C., Jin Q. J. Am. Chem. Soc. 121:1999;54.
4. Furstner A., Weintritt H., Hupperts A. J. Org. Chem. 60:1995;6637.
5. (a) Banwell M., Flynn B., Hamel E., Hockless D. Chem. Commun. 1997;207.
6. (b) Banwell M., Flynn B., Hockless D., Longmore R., Rae D. Aust. J. Chem. 52:1998;755.
7. (c) Banwell M., Flynn B., Hockless D. Chem. Commun. 1997;2259.
8. Heim A., Terpin A., Steglich W. Angew. Chem., Int. Ed. Engl. 36:1997;155.
9. Ishibashi F., Miyazaki Y., Iwao M. Tetrahedron. 53:1997;5951.
10. Liu J., Yang Q., Mak T., Wong H. J. Org. Chem. 65:2000;3587.
11. Quesada A., Gravalos G., Puentes F. Br. J. Cancer. 74:1996;677.
12. (a) Gupton J., Krolikowski D., Riesinger S., Yu R., Sikorski J. J. Org. Chem. 55:1990;4735.
13. (b) Gupton J., Krolikowski D., Yu R., Sikorski J., Vu P., Jones C. J. Org. Chem. 57:1992;5480.
14. (c) Gupton J., Petrich S., Smith L., Bruce M., Vu P., Du K., Dueno E., Jones C., Sikorski J. Tetrahedron. 52:1996;6879.
15. (d) Gupton J., Petrich S., Hicks F., Wilkinson D., Vargas M., Hosein K., Sikorski J. Heterocycles. 47:1998;689.
16. (e) Gupton J., Keertikar K., Krumpe K., Burnham B., Dwornik K., Petrich S., Du K., Bruce M., Vu P., Vargas M., Hosein K., Sikorski J. Tetrahedron. 54:1998;5075.
17. (f) See also Liebscher J., Hartmann H. Synthesis. 1979;241. for a review, which details the applications of chloropropeniminium salts and related derivatives in organic synthesis.
18. Gupton J., Krumpe K., Burnham B., Webb T., Shuford J., Sikorski J. Tetrahedron. 55:1999;14515.
19. Dyke S., Tiley E., White A., Gale D. Tetrahedron. 31:1975;1219.
20. SanMartin R., Marigorta E., Dominguez E. Tetrahedron. 50:1994;2255.
21. Elliot I., Evans S., Kennedy L., Parrish A. Org. Prep. Proced. Int. 21:1989;368.
22. Elliot, I. US patent 5,034,544, July 23, 1991.
23. We are deeply indebted to Mr Dave Patteson of the Biotage Corp. for the donation of a Horizon HPFC flash chromatography system, which was utilized in the final purification of our synthetic Ningalin B hexamethyl ether. We also thank Dr Peter Rahn and Mr Jeff Horsman of the Biotage Corp. for their technical expertise.
24. We would like to thank Professor Dale Boger for providing our research group with NMR, IR and MS spectra of Ningalin B hexamethyl ether.
25. 1H NMR spectra indicative of compounds >95% pure.