Process development of halaven®: Synthesis of the C1-C13 fragment from d -(-)-gulono-1,4-lactone

Synlett

Volumn 24, Issue 3, 2013, Pages 323-326

  Chase, Charles E ^a   Fang, Francis G ^a   Lewis, Bryan M ^a   Wilkie, Gordon D ^a   Schnaderbeck, Matthew J ^a   Zhu, Xiaojie ^a  

^a EISAI INC   (United States)

Author keywords

carbohydrates; chiral pool; drugs; glycosylation; stereo selective synthesis

Indexed keywords

ERIBULIN; GULONO 1,4 LACTONE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; DRUG STRUCTURE; DRUG SYNTHESIS; EPIMERIZATION; PROCESS DEVELOPMENT; PROCESS OPTIMIZATION; QUALITY CONTROL; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 84873411865     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1317919     Document Type: Article

References (19)

1. Uemura D., Takahashi K., Yamamoto T., Katayama C., Tanaka J., Okumura Y., Hirata Y. J. Am. Chem. Soc.: 1985; 107 4796
2. Hirata Y., Uemura D. Pure Appl. Chem.: 1986; 58 701
3. Towle M. J., Salvato K. A., Budrow J., Wels B. F., Kuznetsov G., Aalfs K. K., Welsh S., Zheng W., Seletsky B. M., Palme M. H., Habgood G. J., Singer L. A., DiPietro L. V., Wang Y., Chen J. J., Quincy D. A., Davis A., Yoshimatsu K., Kishi Y., Yu M. J., Littlefield B. A. Cancer Res.: 2001; 61 1013
4. Zheng W., Seletsky B. M., Palme M. H., Lydon P. J., Singer L. A., Chase C. E., Lemelin C. A., Shen Y., Davis H., Tremblay L., Towle M. J., Salvato K. A., Wels B. F., Aalfs K. K., Kishi Y., Littlefield B. A., Yu M. J. Bioorg. Med. Chem. Lett.: 2004; 14 5551
5. Littlefield B. A., Palme M. H., Seletsky B. M., Towle M. J., Yu M. J., Zheng W. US 6214865: 2001
6. Littlefield B. A., Palme M. H., Seletsky B. M., Towle M. J., Yu M. J., Zheng W. US 6365759: 2002
7. Littlefield B. A., Palme M. H., Seletsky B. M., Towle M. J., Yu M. J., Zheng W. WO 9965894: 1999
8. Yu M. J., Kishi Y., Littlefield B. A. In Anticancer Agents from Natural Products. Cragg G. M., Kingston D. G. I, Newman D. J. CRC Press Boca Raton: 2005; 241 265
9. Newman S. Curr. Opin. Invest. Drugs: 2007; 8 1057
10. Vahdat L. T., Pruitt B., Fabian C. J., Rivera R. R., Smith D. A., Tan-Chiu E., Wright J., Tan A. R., DaCosta N. A., Chuang E., Smith J., O'Shaughnessy J., Shuster D. E., Meneses N. L., Chandrawansa K., Fang F., Cole P. E., Ashworth S., Blum J. L. J. Clin. Oncol.: 2009; 27 2954
11. Chiba H., Tagami K. J. Synth. Org. Chem. Jpn.: 2011; 69 600
12. Aicher T. D., Buszek K. R., Fang F. G., Forsyth C. J., Jung S. H., Kishi Y., Matelich M. C., Scola P. M., Spero D. M., Yoon S. K. J. Am. Chem. Soc.: 1992; 114 3162
13. Jackson K. L., Henderson J. A., Motoyoshi H., Phillips A. J. Angew. Chem. Int. Ed.: 2009; 48 2346
14. Yamamoto A., Ueda A., Brémond P., Tiseni P. S., Kishi Y. J. Am. Chem. Soc.: 2012; 134 893
15. Jackson K. L., Henderson J. A., Phillips A. J. Chem. Rev.: 2009; 109 3044; and references therein
16. Duan J. J.-W, Kishi Y. Tetrahedron Lett.: 1993; 34 7541
17. Stamos D. P., Kishi Y. Tetrahedron Lett.: 1996; 37 8643
18. Ishihara K., Karumi Y., Kubota M., Yamamoto H. Synlett: 1996; 839
19. Ishihara K., Kubota M., Kurihara H., Yamamoto H. J. Org. Chem.: 1996; 61 4560