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Volumn , Issue 21, 2007, Pages 2151-2153

Total synthesis of (-)-conocarpan and assignment of the absolute configuration by chemical methods

Author keywords

[No Author keywords available]

Indexed keywords

CONOCARPAN; DIHYDROBENZOFURAN DERIVATIVE; NEOLIGNAN; UNCLASSIFIED DRUG;

EID: 34548221364     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b704211f     Document Type: Article
Times cited : (14)

References (44)
  • 27
    • 34548285232 scopus 로고    scopus 로고
    • We used (-)-diisopropyl tartrate and checked that the material so-labeled was indeed levorotatory See also: ref. 14, page 19
    • We used (-)-diisopropyl tartrate and checked that the material so-labeled was indeed levorotatory
  • 28
    • 84941216140 scopus 로고
    • J. D. Morrison, Academic Press, Orlando, pp 247-308, especially pp 287-288
    • M. G. Finn and K. B. Sharpless, in Asymmetric Synthesis, ed., J. D. Morrison,, Academic Press, Orlando, 1985, vol. 5, pp 247-308
    • (1985) Asymmetric Synthesis, Ed.
    • Finn, M.G.1    Sharpless In, K.B.2
  • 29
    • 0001780886 scopus 로고    scopus 로고
    • We can find only one example of Sharpless epoxidation of a styrene derivative with a para-oxygen substituent (and no additional substituents) on the benzene ring, but it is a kinetic and not a preparative experiment:
    • T. Katsuki V. S. Martin Org. React. 1996 48 1 299
    • (1996) Org. React. , vol.48 , pp. 1-299
    • Katsuki, T.1    Martin, V.S.2
  • 31
    • 34548217575 scopus 로고    scopus 로고
    • -1; 40°C; detection at 210 nm
    • -1; 40°C; detection at 210 nm
  • 33
    • 34548277354 scopus 로고    scopus 로고
    • -1, detection at 232 nm. Baseline separation of a racemic sample; retention times 11.9 min and 14.3 min
    • -1, detection at 232 nm. Baseline separation of a racemic sample; retention times 11.9 min and 14.3 min
  • 35
    • 34548244866 scopus 로고    scopus 로고
    • Opening of related epoxides with phenols did not work in non-aqueous solvents, and diastereoselection in acidic organic solvents was poor; no epoxide opening occurred in basic organic media Cf
    • Opening of related epoxides with phenols did not work in non-aqueous solvents, and diastereoselection in acidic organic solvents was poor; no epoxide opening occurred in basic organic media
  • 37
    • 0037189214 scopus 로고    scopus 로고
    • 13C NMR data for our sample matched the values reported in ref. 4g, 4l and 4c extremely closely, but showed some differences from the values reported in ref. 4a For a related, and sensitive, para-alkoxy allylic carbonate, see compound (R)- 6 in:
    • J. Yu M. J. Gaunt J. B. Spencer J. Org. Chem. 2002 67 4627 4629
    • (2002) J. Org. Chem. , vol.67 , pp. 4627-4629
    • Yu, J.1    Gaunt, M.J.2    Spencer, J.B.3
  • 39
    • 0012815040 scopus 로고
    • Normally, Zn would be required to react with the intermediate iodo epoxide formed from the mesylate. Direct conversion of an iodo epoxide to an allylic alcohol by iodide ion has been suggested in a mechanistic scheme:
    • T. Katsuki K. B. Sharpless J. Am. Chem. Soc. 1980 102 5974 5976
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 5974-5976
    • Katsuki, T.1    Sharpless, K.B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.