Total synthesis of the 5-epimers of naturally occurring (-)-hyacinthacine A5 and unnatural (+)-hyacinthacine A4

Tetrahedron Asymmetry

Volumn 18, Issue 18, 2007, Pages 2211-2217

  Izquierdo, Isidoro ^a   Plaza, María T ^a   Tamayo, Juan A ^a   Sánchez Cantalejo, Fernando ^a  

^a UNIVERSITY OF GRANADA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIHYDROXY 3 HYDROXYMETHYL 5 METHYLPYRROLIZIDINE; 1,2 DIHYDROXY 3 HYDROXYMETHYLPYRROLIZIDINE; 3,4 DIBENZYLOXY N BENZYLOXYCARBONYL 2' O TERT BUTYLDIPHENYLSILYL 2,5 BIS(HYDROXYMETHYL)PYRROLIDINE; 3,4 DIBENZYLOXY N BENZYLOXYCARBONYL 2,5 BIS(HYDROXYMETHYL) 2' O PIVALOYLPYRROLIDINE; 5 EPIHYACINTHACINE A4; 5 EPIHYACINTHACINE A5; ALDEHYDE DERIVATIVE; ALKALOID DERIVATIVE; HYACINTHACINE A4; HYACINTHACINE A5; PYRROLIDINE DERIVATIVE; PYRROLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DEPROTECTION REACTION; EPIMER; HORNER WADSWORTH EMMONS REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS; WITTIG REACTION;

EID: 35148890251     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.09.014     Document Type: Article

References (22)

1. Izquierdo, I.; Plaza, M.-T.; Tamayo, J. A.; Sánchez-Cantalejo, F. Eur. J. Org. Chem. 2007, doi:10.1002/ejoc.200700820.
2. Asano N. Glycobiology 13 (2003) 93R-104R
3. Asano N., Nash R.J., Molyneux R.J., and Fleet G.W.J. Tetrahedron: Asymmetry 11 (2000) 1645-1680
4. Watson A.A., Fleet G.W.J., Asano N., Molyneux R.J., and Nash R.J. Phytochemistry 56 (2001) 265-295
5. Kato A., Adachi I., Miyauchi M., Ikeda K., Komae T., Kizu H., Kameda Y., Watson A.A., Nash R.J., Wormald M.R., Fleet G.W.J., and Asano N. Carbohydr. Res. 316 (1999) 95-103
6. Asano N., Kuroi H., Ikeda K., Kizu H., Kameda Y., Kato A., Adachi I., Watson A.A., Nash R.J., and Fleet G.W.J. Tetrahedron: Asymmetry 11 (2000) 1-8
7. Yamashita T., Yasuda K., Kizu H., Kameda Y., Watson A.A., Nash R.J., Fleet G.W.J., and Asano N. J. Nat. Prod. 65 (2002) 1875-1881
8. Kato A., Kano E., Adachi I., Molyneux R.J., Whatson A.A., Nash R.J., Fleet G.W.J., Wormald M.R., Kizu H., Ikeda K., and Asano N. Tetrahedron: Asymmetry 14 (2003) 325-331
9. Asano N., Ikeda K., Kasahara M., Arai Y., and Kizu H. J. Nat. Prod. 67 (2004) 846-850
10. Kato A., Kato N., Adachi I., Hollinshead J., Fleet G.W.J., Kuriyama Ch., Ikeda K., Asano N., and Nash R.J. J. Nat. Prod. 70 (2007) 993-997
11. Izquierdo I., Plaza M.-T., Robles R., and Franco F. Tetrahedron: Asymmetry 12 (2001) 2481-2487
12. Izquierdo I., Plaza M.T., and Franco F. Tetrahedron: Asymmetry 13 (2002) 1581-1585
13. Izquierdo I., Plaza M.-T., and Franco F. Tetrahedron: Asymmetry 14 (2003) 3933-3935
14. Izquierdo I., Plaza M.-T., and Franco F. Tetrahedron: Asymmetry 15 (2004) 1465-1469
15. Izquierdo I., Plaza M.-T., and Tamayo J.A. Tetrahedron 61 (2005) 6527-6533
16. Izquierdo I., Plaza M.-T., and Tamayo J.A. J. Carbohydr. Chem. 25 (2006) 281-295
17. Izquierdo I., Plaza M.-T., Tamayo J.A., Rodríguez M., and Martos A. Tetrahedron 62 (2006) 6006-6011
18. Zhou L., Chen J., and Cao X.-P. Synthesis (2007) 1359-1365
19. Izquierdo I., Plaza M.-T., Rodríguez M., Franco F., and Martos A. Tetrahedron 61 (2005) 11697-11704
20. Izquierdo I., Plaza M.-T., Rodríguez M., Franco F., and Martos A. Tetrahedron 62 (2006) 1904
21. Izquierdo I., Plaza M.-T., Rodríguez M., Tamayo J.A., and Martos A. Tetrahedron 62 (2006) 2693-2697
22. 13C NMR spectra.