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Volumn 11, Issue 11, 2009, Pages 2285-2288

Manganese(III)-mediated transformations of phloroglucinols: A formal oxidative [4 + 2] cycloaddition leading to bicyclo[2.2.2]octadiones

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; DRUG DERIVATIVE; KETONE; MANGANESE; PHLOROGLUCINOL;

EID: 66149171363     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900590t     Document Type: Article
Times cited : (47)

References (48)
  • 4
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    • Snider, B. B.; Mohan, R.; Kates, S. A J. Org. Chem. 1985, 50, 3659.
    • Snider, B. B.; Mohan, R.; Kates, S. A J. Org. Chem. 1985, 50, 3659.
  • 33
    • 66149167236 scopus 로고    scopus 로고
    • See the Supporting Information for complete experimental details
    • See the Supporting Information for complete experimental details.
  • 34
    • 0142248451 scopus 로고    scopus 로고
    • For previous use of Mn(III)-based oxidative cyclization toward phloroglucinol natural products, see: Kraus, G. A.; Dneprovskaia, E.; Nguyen, T. H.; Jeon, I. Tetrahedron 2003, 59, 8975.
    • For previous use of Mn(III)-based oxidative cyclization toward phloroglucinol natural products, see: Kraus, G. A.; Dneprovskaia, E.; Nguyen, T. H.; Jeon, I. Tetrahedron 2003, 59, 8975.
  • 35
    • 66149192328 scopus 로고    scopus 로고
    • In the 1H NMR spectra of dearomatized benzoylphloroglucinol derivatives such as 3, the enolic hydrogen appears in the far downfield region (16-18 ppm) suggesting complete enolization. The compound exists as a mixture of two enol tautomers. See ref 1a,d for a discussion on the mechanistic details of Mn(III)-based oxidations of 1,3-dicarbonyl compounds
    • In the 1H NMR spectra of dearomatized benzoylphloroglucinol derivatives such as 3, the enolic hydrogen appears in the far downfield region (16-18 ppm) suggesting complete enolization. The compound exists as a mixture of two enol tautomers. See ref 1a,d for a discussion on the mechanistic details of Mn(III)-based oxidations of 1,3-dicarbonyl compounds.
  • 36
    • 0004032955 scopus 로고
    • Kochi, J. K, Ed, Wiley: New York, Chapter 11
    • Kochi; J. K. In Free Radicals; Kochi, J. K., Ed.; Wiley: New York, 1973; Vol. 1, Chapter 11.
    • (1973) Free Radicals , vol.1
    • Kochi, J.K.1
  • 45
    • 66149189239 scopus 로고    scopus 로고
    • These products appear to result from multiple cyclization modes onto the tetrasubstituted olefin (O vs C, 6-endo vs 5-exo).
    • These products appear to result from multiple cyclization modes onto the tetrasubstituted olefin (O vs C, 6-endo vs 5-exo).
  • 46
    • 33846179321 scopus 로고    scopus 로고
    • Attempts to use non-allylic bromides led to low reactivity mainly resulting in alkylation of the phenolic oxygens. The alkyl triflate was prepared using a modified literature procedure: Bashore, C. G, Vetelino, M. G, Wirtz, M. C, Brooks, P. R, Frost, H. N, McDermott, R. E, Whritenour, D. C, Ragan, J. A, Rutherford, J. L, Makowski, T. W, Brenek, S. J, Coe, J. W. Org. Lett. 2006, 8, 5947
    • Attempts to use non-allylic bromides led to low reactivity mainly resulting in alkylation of the phenolic oxygens. The alkyl triflate was prepared using a modified literature procedure: Bashore, C. G.; Vetelino, M. G.; Wirtz, M. C.; Brooks, P. R.; Frost, H. N.; McDermott, R. E.; Whritenour, D. C.; Ragan, J. A.; Rutherford, J. L.; Makowski, T. W.; Brenek, S. J.; Coe, J. W. Org. Lett. 2006, 8, 5947.
  • 47
    • 66149192329 scopus 로고    scopus 로고
    • Enones 25, 26, and 28 were isolated as a single (Z) isomer (1H NMR).
    • Enones 25, 26, and 28 were isolated as a single (Z) isomer (1H NMR).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.