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Volumn 74, Issue 23, 2009, Pages 9140-9151

Development of an oxazole conjunctive reagent and application to the total synthesis of siphonazoles

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL ACTIVITIES; BUILDING BLOCKES; CHEMICAL EQUATIONS; NATURAL PRODUCTS; OXAZOLES; TOTAL SYNTHESIS;

EID: 72249118391     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9018705     Document Type: Article
Times cited : (40)

References (133)
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    • For higher polyoxazoles of this type, see the following leading references
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    • This substructure is characteristic of the bengazoles, a group of about 20 marine substances with remarkable bioactivity. Isolation
    • This substructure is characteristic of the bengazoles, a group of about 20 marine substances with remarkable bioactivity. Isolation: (a) Adamczeski, M.; Quinoa, E.; Crews, P. J. Am. Chem. Soc. 1988, 110, 1598.
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    • This paper provides a thorough bibliography of oxazole-forming reactions through early 2003
    • Coqueron, P. Y.; Didier, C.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2003, 42, 1411. This paper provides a thorough bibliography of oxazole-forming reactions through early 2003.
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    • It is important to note that among these methods only the chemistry of refs 10 and 13 permits access to the 2,5-dialkyloxazole-4-carboxylate series
    • (e) Merkul, E.; Grotkopp, O.; Müller, T. J. J. Synthesis 2009, 502. It is important to note that among these methods only the chemistry of refs 10 and 13 permits access to the 2,5-dialkyloxazole-4-carboxylate series.
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    • The preparation of this material is provided as Supporting Information
    • The preparation of this material is provided as Supporting Information.
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    • This is imputable to the unfavorable positioning of the 4-COOR substituent: the 5-COOR isomer is smoothly deprotonated at the C-2 Me group (ref 24), presumably because of good resonance stabilization of the ensuing anion
    • This is imputable to the unfavorable positioning of the 4-COOR substituent: the 5-COOR isomer is smoothly deprotonated at the C-2 Me group (ref 24), presumably because of good resonance stabilization of the ensuing anion.
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    • Conceivably, 56 could be made by Rh(II)-mediated condensation of diethyl cyanomethyl-phosphonate with ethyl diazoacetoacetate according to Hoffmann, et al. (ref 27b). However, the modest yield (18%) obtained by these authors in a similar reaction of phosphonoacetonitrile with diethyl diazomalonate discouraged us from researching this possibility
    • Conceivably, 56 could be made by Rh(II)-mediated condensation of diethyl cyanomethyl-phosphonate with ethyl diazoacetoacetate according to Hoffmann, et al. (ref 27b). However, the modest yield (18%) obtained by these authors in a similar reaction of phosphonoacetonitrile with diethyl diazomalonate discouraged us from researching this possibility.
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    • The following patents describe the preparation of some 2-(arylsulfonyl)methyloxazole-4-carboxylic esters: JP 59108772 A 19840623 Showa (Taiho Pharmaceutical Co., Ltd.), CAN 101:171238
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    • However, this study also revealed that a Wadsworth-Emmons olefination mode is distinctly superior
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    • For an excellent discussion of the vinylsulfone-allylsulfone isomerization, see: and literature cited therein. See especially pp 2331 ff
    • For an excellent discussion of the vinylsulfone-allylsulfone isomerization, see: El-Awa, A.; Noshi, M. N.; Mollat du Jourdin, X.; Fuchs, P. L. Chem. Rev. 2009, 109, 2315 and literature cited therein. See especially pp 2331 ff.
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    • N,N′-Carbonyldiimidazole
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    • 13C signal at 85 ppm. See the spectra provided in the Supporting Information
    • 13C signal at 85 ppm. See the spectra provided in the Supporting Information.
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    • 6 solutions
    • 6 solutions.
  • 132
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    • Relevant experimental protocols are provided as Supporting Information
    • Relevant experimental protocols are provided as Supporting Information.
  • 133
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    • Additional details are provided as Supporting Information
    • Additional details are provided as Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.