Synthesis of sporiolide B from d-glucal

Carbohydrate Research

Volumn 342, Issue 11, 2007, Pages 1405-1411

  Chen, Qi ^a   Du, Yuguo ^a  

^a RESEARCH CENTER FOR ECO ENVIRONMENTAL SCIENCES   (China)

Author keywords

d Glucal; Macrolides; Natural products; Sporiolide B; Total synthesis

Indexed keywords

D-GLUCAL; MITSUNOBU REACTION; NATURAL MACROLIDE; SPORIOLIDE B;

ESTERIFICATION; GLUCOSE; STEREOCHEMISTRY;

SYNTHESIS (CHEMICAL);

GLUCONATE CALCIUM; MACROLIDE; SPORIOLIDE B; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ESTERIFICATION; MITSUNOBU REACTION; PRIORITY JOURNAL; RING CLOSING METATHESIS; STEREOCHEMISTRY;

ALGAE, RED; ANTI-BACTERIAL AGENTS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DEOXYGLUCOSE; GROWTH INHIBITORS; HELA CELLS; HUMANS; LACTONES; MACROLIDES;

EID: 34250643160     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2007.04.013     Document Type: Article

References (28)

1. Blunt J.W., Copp B.R., Munro M.H.G., Northcote P.T., and Prinsep M.R. Nat. Prod. Rep. 21 (2004) 1-49
2. Faulkner D. Nat. Prod. Rep. 19 (2002) 1-48
3. Blunt J.W., Copp B.R., Munro M.H.G., Northcote P.T., and Prinsep M.R. Nat. Prod. Rep. 22 (2005) 15-61
4. Blunt J.W., Copp B.R., Munro M.H.G., Northcote P.T., and Prinsep P.R. Nat. Prod. Rep. 23 (2006) 26-78
5. Tsuda M., Mugishima T., Komatsu K., Sone T., and Tanaka M. J. Nat. Prod. 66 (2003) 412-415
6. Gesner S., Cohen N., Iian M., Yarden O., and Carmeli S. J. Nat. Prod. 68 (2005) 1350-1353
7. Shigemori H., Kasai Y., Komatsu K., Tsuda M., Mikami Y., and Kobayashi J. Mar. Drugs 2 (2004) 164-169
8. Chen Q., and Du Y. Tetrahedron Lett. 47 (2006) 8489-8492
9. Schell P., Orgueira H.A., Roehrig S., and Seeberger P.H. Tetrahedron Lett. 42 (2001) 3811-3814
10. Riley A.M., Jenkins D.J., Marwood R.D., and Potter B.V.L. Carbohydr. Res. 337 (2002) 1067-1082
11. Joniak D., Košíková B., and Kosáková L. Collect. Czech. Chem. Commun. 43 (1978) 769-773
12. Johanssonm R., and Samuelsson B. J. Chem. Soc., Perkin Trans. 1 (1984) 2371-2374
13. Du Y., Chen Q., and Linhardt R.J. J. Org. Chem. 71 (2006) 8446-8451
14. Rollin P., and Sinaÿ P. Carbohydr. Res. 98 (1981) 139-142
15. Roth B.D., and Roark W.H. Tetrahedron Lett. 29 (1988) 1255-1258
16. Baba T., Huang G., and Isobe M. Tetrahedron 59 (2003) 6851-6872
17. Piancatelli G., Scettri A., and D'Auria M. Tetrahedron Lett. 18 (1977) 3483-3484
18. Mitsunobu O. Synthesis (1981) 1-28
19. Ahn C., Correia R., and DeShong P. J. Org. Chem. 67 (2002) 1751-1753 and references cited therein
20. Du Y., Liu J., and Linhardt R.J. J. Org. Chem. 71 (2006) 1251-1253
21. Takahata H., Yotsui Y., and Momose T. Tetrahedron 54 (1998) 13505-13516
22. Inanaga J., Hirata K., Saeki H., Katsuki T., and Yamaguchi M. Bull. Chem. Soc. Jpn. 52 (1979) 1989-1993
23. Oikawa Y., Tanaka T., Horita K., and Yonemitsu O. Tetrahedron Lett. 25 (1984) 5397-5400
24. Tanaka T., Oikawa Y., Hamada T., and Yonemitsu O. Tetrahedron Lett. 27 (1986) 3651-3654
25. Dess P.B., and Martin J.C. J. Org. Chem. 48 (1983) 4155-4156
26. Grubbs R.H., and Chang S. Tetrahedron 54 (1998) 4413-4450
27. Kuroda I., Musman M., Ohtani I.I., Ichiba T., Tanaka J., Cravalos D.C., and Higa T. J. Nat. Prod. 65 (2002) 1505-1506
28. Ledroit V., Debitus C., Lavaud C., and Massiot G. Tetrahedron Lett. 44 (2003) 225-228