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Volumn 12, Issue 15, 2010, Pages 3453-3455

Total synthesis of syringolin A

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CYCLOPEPTIDE; SYRINGOLIN A; VALINE;

EID: 77955136605     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101252y     Document Type: Article
Times cited : (39)

References (34)
  • 8
    • 77955159713 scopus 로고    scopus 로고
    • For a discussion of the proteasome as a target for cancer chemotherapy, see
    • For a discussion of the proteasome as a target for cancer chemotherapy, see
  • 20
    • 77955163060 scopus 로고    scopus 로고
    • The stereochemical integrity of the α-stereogenic center and % ee of 7 were determined by HPLC analysis
    • The stereochemical integrity of the α-stereogenic center and % ee of 7 were determined by HPLC analysis.
  • 21
    • 85023346540 scopus 로고
    • For seminal studies on the preparation and utility of vinylogous amino acids, see
    • For seminal studies on the preparation and utility of vinylogous amino acids, see: Hagihara, M.; Anthony, N. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6568
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 6568
    • Hagihara, M.1    Anthony, N.J.2    Stout, T.J.3    Clardy, J.4    Schreiber, S.L.5
  • 23
    • 77955124625 scopus 로고    scopus 로고
    • During the preparation of this manuscript, Kaiser and coworkers described a similar approach to fragment 4; see ref 9b
    • During the preparation of this manuscript, Kaiser and coworkers described a similar approach to fragment 4; see ref 9b.
  • 24
    • 77955149807 scopus 로고    scopus 로고
    • 1H NMR
    • 1H NMR.
  • 25
    • 77955165599 scopus 로고    scopus 로고
    • Decomposition and epimerization were always observed when handling the aldehyde. In contrast, the carboxylic acid was found to be quite stable and did not undergo noticeable epimerization
    • Decomposition and epimerization were always observed when handling the aldehyde. In contrast, the carboxylic acid was found to be quite stable and did not undergo noticeable epimerization.
  • 26
    • 77955152707 scopus 로고    scopus 로고
    • For an example of the lability of the products of oxidation of vinylglycinol derivatives, see
    • For an example of the lability of the products of oxidation of vinylglycinol derivatives, see
  • 28
    • 77955169083 scopus 로고    scopus 로고
    • 1H NMR as compared with the coupling of 4 with (±)-α- methylbenzylamine. See Supporting Information for further details
    • 1H NMR as compared with the coupling of 4 with (±)-α- methylbenzylamine. See Supporting Information for further details.
  • 29
    • 77955137245 scopus 로고    scopus 로고
    • This intermediate was also prepared in the recently reported synthesis by Pirrung and coworkers using a Horner-Wadsworth-Emmons macrocyclization. See ref 10 for details
    • This intermediate was also prepared in the recently reported synthesis by Pirrung and coworkers using a Horner-Wadsworth-Emmons macrocyclization. See ref 10 for details.
  • 30
    • 77955154785 scopus 로고    scopus 로고
    • Analysis of the crude UPLC-MS data indicated that dimeric and trimeric products are also formed during the formation of the strained 12-membered macrocycle
    • Analysis of the crude UPLC-MS data indicated that dimeric and trimeric products are also formed during the formation of the strained 12-membered macrocycle.
  • 31
    • 77955145780 scopus 로고    scopus 로고
    • The isocyanate was prepared using triphosgene; see
    • The isocyanate was prepared using triphosgene; see
  • 34
    • 77955167597 scopus 로고    scopus 로고
    • note
    • + 494.2979, found 494.3003.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.