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Volumn , Issue 2, 1997, Pages 202-206

Synthesis of (E,E,E)-(1,2,3,4-13C4)-geranylgeraniol

Author keywords

(1,2,3,4 13C4) ethyl acetoacetate; 13C labelled compounds; chain elongation; geranylgeraniol; protein lipidation

Indexed keywords

CARBON 13; GERANYLGERANIOL; TERPENOID; UNCLASSIFIED DRUG;

EID: 0031040491     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1154     Document Type: Article
Times cited : (18)

References (27)
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    • Davisson, V. J.; Woodside, A. B.; Poulter, C. D. Methods Enzymol. 1985, 110, 130. Davisson, V. J.; Woodside, A. B.; Neal, T. R.; Stremler, K. E.; Muehlbacher, M.; Poulter, C. D. J. Org. Chem. 1986, 51, 4768. Woodside, A. B.; Huang, Z.; Poulter, C. D. Org. Synth. 1988, 66, 211.
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    • note
    • 1H NMR spectroscopy. Separation was achieved at this stage via preparative TLC.
  • 20
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    • Sum, F.-W.; Weiler, L. Can. J. Chem. 1979, 57, 1431. Huckin, S. N.; Weiler, L. J. Am. Chem. Soc. 1974, 96, 1082.
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    • note
    • 4 afforded a 2:1 mixture of 2 and its 2,3-dihydro derivative.
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    • While our work was in progress, Mu and Gibbs (Mu, Y.-Q.; Gibbs, R. A. Tetrahedron Lett. 1995, 36, 5669) communicated a somewhat related method for the conversion of 3 to 2 which also follows the Sum/Weiler strategy (27 % overall yield). Instead of the enol phosphate 13, these authors used the corresponding enol triflate which was converted to 14 via Suzuki coupling.
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    • This material is commercially available from Cambridge Isotope Laboratories, Inc.
    • This material is commercially available from Cambridge Isotope Laboratories, Inc..


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.