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Volumn 11, Issue 11, 2009, Pages 2389-2392

Total synthesis of siphonazoles by the use of a conjunctive oxazole building block

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; OXAZOLE DERIVATIVE; SIPHONAZOLE;

EID: 66149172044     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900455m     Document Type: Article
Times cited : (59)

References (55)
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    • Cornwall, P. Dell, C. P. Knight, D. W. J. Chem. Soc., Perkin Trans. 1 1991, 2417. These authors report that under particular conditions it is possible to generate a 1:1 mixture C-2 and C-4 lithiomethyl derivatives of the oxazole 4-carboxylic acid.
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    • These difficulties may be ascribed to the unfavorable positioning of the 4-COOR substituent: the 5-COOR isomer is smoothly deprotonated at the C-2 Me group (ref 7), arguably because of good mesomeric stabilization of the resulting anion. In a later step of the synthesis of 1 and 2 (ref 2), Moody bypassed the problem by employing an organozinc reagent prepared from the 2-
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    • analogue of oxazole 8.
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    • Reference a above contains an extensive bibliography of oxazole-forming reactions. Subsequent representative examples of oxazole construction via the cyclization of N-propargylamide intermediates
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    • It is important to note that among these methods only the chemistry of refs a and b permits access to the 2,5-dialkyloxazole-4-carboxylate series
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    • The deprotonation of 22 with NaH is in accord with ref 6.
    • The deprotonation of 22 with NaH is in accord with ref 6.
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    • These results shall be detailed in a forthcoming full paper.
    • These results shall be detailed in a forthcoming full paper.
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    • The enol tautomer of 1-2 was recognizable from a characteristic 13C signal at 85 ppm. See the spectra provided in the Supporting Information.
    • The enol tautomer of 1-2 was recognizable from a characteristic 13C signal at 85 ppm. See the spectra provided in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.