A new synthesis of tanikolide

Tetrahedron Letters

Volumn 44, Issue 14, 2003, Pages 2893-2894

  Zhai, Hongbin ^a   Chen, Qingshou ^a   Zhao, Jingrui ^a,b   Luo, Shengjun ^a   Jia, Xueshun ^b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b SHANGHAI UNIVERSITY   (China)

Author keywords

Marine natural products; Synthesis; Tanikolide

Indexed keywords

ANTIFUNGAL AGENT; CARBOXYLIC ACID DERIVATIVE; ETHYL 2 OXOCYCLOPENTANECARBOXYLATE; TANIKOLIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; BAEYER VILLIGER REACTION; CHEMICAL REACTION; DRUG SYNTHESIS; GRIGNARD REACTION; LACTONIZATION; REDUCTION; SAPONIFICATION;

EID: 0037474611     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00450-7     Document Type: Article

References (15)

1. Singh I.P., Milligan K.E., Gerwick W.H. J. Nat. Prod. 62:1999;1333.
2. Kanada R.M., Taniguchi T., Ogasawara K. Synlett. 2000;1019.
3. Wan Z., Nelson S.G. J. Am. Chem. Soc. 122:2000;10470.
4. Chang M.-Y., Lin C.-L., Chen S.-T. J. Chin. Chem. Soc. 48:2001;787.
5. Krauss J. Nat. Prod. Lett. 15:2001;393.
6. Venton D.L., Enke S.E., Le Breton G.C. J. Med. Chem. 22:1979;824.
7. Williams T.R., Sirvio L.M. J. Org. Chem. 45:1980;5082.
8. Teixeira L.H.P., Barreiro E.J., Fraga C.A.M. Synth. Commun. 27:1997;3241 The alkylation product 2 was reportedly synthesized in 55% yield from the sodium salt of ethyl 2-oxocyclopentanecarboxylate. Maillard, A.; Deluzarche, A.; Rudloff, A. Compt. Rend. 1955, 240, 317; Chem. Abstr. 1956, 50, 1615e.
9. Nishimura Y., Mori K. Eur. J. Org. Chem. 2:1998;233-236.
10. White J.D., Amedio J.C. Jr., Gut S., Ohira S., Jayasinghe L.R. J. Org. Chem. 57:1992;2270.
11. Alexandre F., Legoupy S., Huet F. Tetrahedron. 56:2000;3921.
12. 3: C, 71.79; H, 11.34. Found: C, 71.64; H, 10.98.
13. Kraus G.A., Frazier K. J. Org. Chem. 45:1980;4262.
14. Matsuo K., Kinuta T., Tanaka K. Chem. Pharm. Bull. 29:1981;3047.
15. Suemune H., Harabe T., Xie Z.-F., Sakai K. Chem. Pharm. Bull. 36:1988;4337.