Permanganate oxidation of 1,5,9-trienes: Stereoselective synthesis of tetrahydrofuran-containing fragments

Journal of Organic Chemistry

Volumn 67, Issue 23, 2002, Pages 8079-8085

  Brown, Richard C D ^a   Bataille, Carole J ^a   Hughes, Robert M ^a   Kenney, Anne ^a   Luker, Tim J ^b  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

STEREOCENTERS;

ANTIBIOTICS; ESTERS; OXIDATION; POLYETHERS; SYNTHESIS (CHEMICAL);

STEREOCHEMISTRY;

ANTIBIOTIC AGENT; CAROLIN A; ETHYL 2 HYDROXY 2 (2',5 DIMETHYL 5' OXOOCTAHYDRO[2,2']BIFURANYL 5 YL)ETHANOATE; ETHYL 2 HYDROXY 2 [5' HYDROXY 5' (1 HYDROXY 1 METHYLETHYL) 5,2' DIMETHYLOCTAHYDRO[2.2']BIFURANYL 5 YL]ETHANOATE; ETHYL 3,7,11 TRIMETHYL 2,6,10 DODECATRIENOATE; PERMANGANATE POTASSIUM; POLYETHER DERIVATIVE; SEMDURAMYCIN; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG; FARNESOIC ACID; FURAN DERIVATIVE; POLYENE; UNSATURATED FATTY ACID;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; STEREOCHEMISTRY; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

FATTY ACIDS, UNSATURATED; FURANS; OXIDATION-REDUCTION; POLYENES; POTASSIUM PERMANGANATE; STEREOISOMERISM;

EID: 0037111702     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026295b     Document Type: Article

References (34)

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10. For studies on the permanganate-mediated oxidative cyclization of 1,5-dienes see: (a) Kötz, A.; Steche, T. J. Prakt. Chem. 1924, 107, 193. (b) Klein, E.; Rojahn, W. Tetrahedron 1979, 21, 2353-2358. (c) Walba, D. M.; Wand, M. D.; Wilkes, M. C. J. Am. Chem. Soc. 1979, 101, 4396-4397. (d) Baldwin, J. E.; Crossley, M. J.; Lehtonen, E.-M. M. J. Chem. Soc., Chem. Commun. 1979, 918-919. (e) Wolfe, S.; Ingold, C. F. J. Am. Chem. Soc. 1981, 103, 940-941.
11. For studies on the permanganate-mediated oxidative cyclization of 1,5-dienes see: (a) Kötz, A.; Steche, T. J. Prakt. Chem. 1924, 107, 193. (b) Klein, E.; Rojahn, W. Tetrahedron 1979, 21, 2353-2358. (c) Walba, D. M.; Wand, M. D.; Wilkes, M. C. J. Am. Chem. Soc. 1979, 101, 4396-4397. (d) Baldwin, J. E.; Crossley, M. J.; Lehtonen, E.-M. M. J. Chem. Soc., Chem. Commun. 1979, 918-919. (e) Wolfe, S.; Ingold, C. F. J. Am. Chem. Soc. 1981, 103, 940-941.
12. For earlier applications of the permanganate-promoted oxidative cyclization of 1,5-dienes to the synthesis of fragments of polyether antibiotics monensin, ionomycin, and salinomycin see: (a) Walba, D. M.; Edwards, P. D. Tetrahedron Lett. 1980, 21, 3531-3534. (b) Spino, C.; Weiler, L. Tetrahedron Lett. 1987, 28, 731-734. (c) Walba, D. M.; Przybyla, C. A.; Walker, C. B. J. J. Am. Chem. Soc. 1990, 112, 5624-5625. (d) Brown, R. C. D.; Kocienski, P. J. Syn. Lett. 1994, 415-417. (e) Kocienski, P. J.; Brown, R. C. D.; Pommier, A.; Procter, M.; Schmidt, B. J. Chem. Soc., Perkin Trans. 1 1998, 9-39. (f) Cecil, A. R. L.; Brown, R. C. D. Org. Lett. 2002, 4, 3715-3718.
13. For earlier applications of the permanganate-promoted oxidative cyclization of 1,5-dienes to the synthesis of fragments of polyether antibiotics monensin, ionomycin, and salinomycin see: (a) Walba, D. M.; Edwards, P. D. Tetrahedron Lett. 1980, 21, 3531-3534. (b) Spino, C.; Weiler, L. Tetrahedron Lett. 1987, 28, 731-734. (c) Walba, D. M.; Przybyla, C. A.; Walker, C. B. J. J. Am. Chem. Soc. 1990, 112, 5624-5625. (d) Brown, R. C. D.; Kocienski, P. J. Syn. Lett. 1994, 415-417. (e) Kocienski, P. J.; Brown, R. C. D.; Pommier, A.; Procter, M.; Schmidt, B. J. Chem. Soc., Perkin Trans. 1 1998, 9-39. (f) Cecil, A. R. L.; Brown, R. C. D. Org. Lett. 2002, 4, 3715-3718.
14. For earlier applications of the permanganate-promoted oxidative cyclization of 1,5-dienes to the synthesis of fragments of polyether antibiotics monensin, ionomycin, and salinomycin see: (a) Walba, D. M.; Edwards, P. D. Tetrahedron Lett. 1980, 21, 3531-3534. (b) Spino, C.; Weiler, L. Tetrahedron Lett. 1987, 28, 731-734. (c) Walba, D. M.; Przybyla, C. A.; Walker, C. B. J. J. Am. Chem. Soc. 1990, 112, 5624-5625. (d) Brown, R. C. D.; Kocienski, P. J. Syn. Lett. 1994, 415-417. (e) Kocienski, P. J.; Brown, R. C. D.; Pommier, A.; Procter, M.; Schmidt, B. J. Chem. Soc., Perkin Trans. 1 1998, 9-39. (f) Cecil, A. R. L.; Brown, R. C. D. Org. Lett. 2002, 4, 3715-3718.
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