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Volumn 64, Issue 25, 1999, Pages 9178-9188

Total synthesis of dihydroclerodin from (R)-(-)-carvone

Author keywords

[No Author keywords available]

Indexed keywords

CARVONE; DIHYDROCLERODIN; INSECTICIDE; LUPULIN C; UNCLASSIFIED DRUG;

EID: 0032804353     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991151r     Document Type: Article
Times cited : (44)

References (55)
  • 28
    • 0003017597 scopus 로고
    • Chapman & Hall: New York
    • Throughout the discussion the numbering of the clerodane skeleton is followed as given by Connolly, J. D.; Hill, R. A. Dictionary of Terpenoids; Chapman & Hall: New York, 1991; Vol. 1, pp XXXII.
    • (1991) Dictionary of Terpenoids , vol.1
    • Connolly, J.D.1    Hill, R.A.2
  • 33
    • 0344555860 scopus 로고    scopus 로고
    • X-ray crystallography was done by Veldman, N.; Menzer, S.; Spek, A. L. Bijvoet Center for Biomolecular Research, Department of Crystal and Structural Chemistry, Utrecht University
    • X-ray crystallography was done by Veldman, N.; Menzer, S.; Spek, A. L. Bijvoet Center for Biomolecular Research, Department of Crystal and Structural Chemistry, Utrecht University.
  • 38
    • 0344986830 scopus 로고    scopus 로고
    • note
    • To prevent this base-catalyzed isomerization the less basic organocerium reagent was studied in the addition reaction, but this did not yield the addition product due to the low reactivity of the organocerium reagent.
  • 40
    • 0344555851 scopus 로고    scopus 로고
    • note
    • PPTS was used as a catalyst for the aldol condensation, because the more acidic PTSA yielded many side products (see also note 26).
  • 42
    • 0344124291 scopus 로고
    • For similar fast trapping of enolates by oxygen, see: (a) Koreeda, M.; You, Z. J. Org. Chem. 1989, 54, 5195-5198. (b) Gallagher, T. F.; Adams, J. L. J. Org. Chem. 1992, 57, 3347-3353.
    • (1989) J. Org. Chem. , vol.54 , pp. 5195-5198
    • Koreeda, M.1    You, Z.2
  • 43
    • 0343760145 scopus 로고
    • For similar fast trapping of enolates by oxygen, see: (a) Koreeda, M.; You, Z. J. Org. Chem. 1989, 54, 5195-5198. (b) Gallagher, T. F.; Adams, J. L. J. Org. Chem. 1992, 57, 3347-3353.
    • (1992) J. Org. Chem. , vol.57 , pp. 3347-3353
    • Gallagher, T.F.1    Adams, J.L.2
  • 45
    • 0345418017 scopus 로고    scopus 로고
    • note
    • 3 during NMR recording to give a triol.
  • 46
  • 50
    • 9444231182 scopus 로고    scopus 로고
    • This compound is isolated from Ajuga lupulina. Chen, H.; Tan, R. X.; Liu, Z. L.; Zhang, Y. J. Nat. Prod. 1996, 59, 668-670. However, their reported fragment peaks are not in accordance with the ones we found.
    • (1996) J. Nat. Prod. , vol.59 , pp. 668-670
    • Chen, H.1    Tan, R.X.2    Liu, Z.L.3    Zhang, Y.4
  • 51
    • 0344986829 scopus 로고    scopus 로고
    • note
    • 3 and MeOH. See also ref 18. (equation presented)
  • 55
    • 84988124106 scopus 로고
    • Schlosser, M.; Jenny, T.; Guggisberg, Y. Synlett 1990, 704. For oxygen free, a cooled solution of THF, paraformaldehyde, and acid was degassed prior to slowly distillation under argon.
    • (1990) Synlett , pp. 704
    • Schlosser, M.1    Jenny, T.2    Guggisberg, Y.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.