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Volumn 125, Issue 6, 2003, Pages 1567-1574

Concise total syntheses of the bioactive mesotricyclic diterpenoids jatrophatrione and citlalitrione

Author keywords

[No Author keywords available]

Indexed keywords

METHYLATION;

EID: 0037433270     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja021177r     Document Type: Article
Times cited : (41)

References (58)
  • 6
    • 0037067076 scopus 로고    scopus 로고
    • For a preliminary communication delineating our concise approach to jatrophatrione, consult Paquette, L. A.; Yang, J.; Long, Y. O. J. Am. Chem. Soc. 2002, 124, 6542.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 6542
    • Paquette, L.A.1    Yang, J.2    Long, Y.O.3
  • 9
    • 0001696551 scopus 로고
    • The feasibility of attaining stereocontrol by rotation around the σ bonds flanking an olefinic linkage has been previously demonstrated by us in a tricyclic precursor to taxusin: (a) Paquette, L. A.; Zhao, M. J. Am. Chem. Soc. 1993, 115, 354. (b) Paquette, L. A.; Zhao, M. J. Am. Chem. Soc. 1998, 120, 5203.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 354
    • Paquette, L.A.1    Zhao, M.2
  • 10
    • 0032478976 scopus 로고    scopus 로고
    • The feasibility of attaining stereocontrol by rotation around the σ bonds flanking an olefinic linkage has been previously demonstrated by us in a tricyclic precursor to taxusin: (a) Paquette, L. A.; Zhao, M. J. Am. Chem. Soc. 1993, 115, 354. (b) Paquette, L. A.; Zhao, M. J. Am. Chem. Soc. 1998, 120, 5203.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 5203
    • Paquette, L.A.1    Zhao, M.2
  • 31
    • 0346945823 scopus 로고    scopus 로고
    • note
    • 4 in the absence of Cul and HMPA afforded 26 in only 11% yield.
  • 36
    • 0000020181 scopus 로고
    • Wiley: New York, Collect.
    • (b) Abrams, S. R.; Shaw, A. C. Organic Syntheses; Wiley: New York, 1993: Collect. Vol. VIII, p 146.
    • (1993) Organic Syntheses , vol.8 , pp. 146
    • Abrams, S.R.1    Shaw, A.C.2
  • 40
    • 0003905731 scopus 로고
    • Academic Press: New York. Chapt. 6
    • Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York. 1984; Vol. 3B, Chapt. 6.
    • (1984) Asymmetric Synthesis , vol.3 B
    • Bartlett, P.A.1
  • 51
    • 0346315727 scopus 로고    scopus 로고
    • note
    • 2, or HMPA, the allylic mercury intermediate was the only product isolated. The generation of this species appears to be rapid in all media. The ensuing step in which Hg(II) is reduced to Hg(0) is believed to be the rate-determining step. If so, the role of nonpolar benzene is to stabilize the transition state and accelerate the overall rate.
  • 56
    • 0346315726 scopus 로고    scopus 로고
    • Unpublished observations in this laboratory
    • Yang, J. Unpublished observations in this laboratory.
    • Yang, J.1
  • 57
    • 0347576697 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum or a sample of natural jatrophatrione, Professor Robert Bates responded (letter dated December 15, 1995) that neither could be located at that time.
  • 58
    • 0346315725 scopus 로고    scopus 로고
    • Footnote 15 of ref 4
    • Footnote 15 of ref 4.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.