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Volumn 72, Issue 1, 1999, Pages 85-97

Synthesis of medium-sized bicyclic compounds by intramolecular cyclization of cyclic β-keto radicals generated from cyclopropanols using manganese(III) tris(pyridine-2-carboxylate) and its application to total synthesis of 10-isothiocyanatoguaia-6-ene

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BICYCLO COMPOUND; CYCLOPROPANE DERIVATIVE; ISOTHIOCYANIC ACID DERIVATIVE; MANGANESE DERIVATIVE; PICOLINIC ACID DERIVATIVE; RADICAL; SELENIDE; SESQUITERPENE DERIVATIVE; TRIBUTYLTIN;

EID: 0032891037     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.72.85     Document Type: Article
Times cited : (35)

References (77)
  • 17
    • 0029987404 scopus 로고    scopus 로고
    • b) B. M. Franga, Nat. Prod. Rep., 13, 307 (1996); 14, 145 (1997); 15, 73 (1998).
    • (1996) Nat. Prod. Rep. , vol.13 , pp. 307
    • Franga, B.M.1
  • 18
    • 0030939920 scopus 로고    scopus 로고
    • b) B. M. Franga, Nat. Prod. Rep., 13, 307 (1996); 14, 145 (1997); 15, 73 (1998).
    • (1997) Nat. Prod. Rep. , vol.14 , pp. 145
  • 19
    • 0039373838 scopus 로고    scopus 로고
    • b) B. M. Franga, Nat. Prod. Rep., 13, 307 (1996); 14, 145 (1997); 15, 73 (1998).
    • (1998) Nat. Prod. Rep. , vol.15 , pp. 73
  • 24
    • 0000315424 scopus 로고
    • Radical cyclizations and sequential radical reactions
    • ed by B. M. Trost, Pergamon Press, New York
    • c) D. P. Curran, "Radical Cyclizations and Sequential Radical Reactions," in "Comprehensive Organic Synthesis," ed by B. M. Trost, Pergamon Press, New York (1991), Vol. 4, p. 779.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 779
    • Curran, D.P.1
  • 28
    • 0013503358 scopus 로고    scopus 로고
    • note
    • The reaction was carried out employing a mixture of diastereomeric cyclopropanols. It was expected that either isomer produced the same β-keto radical.
  • 41
    • 0013468957 scopus 로고    scopus 로고
    • note
    • 11b) MM2 calculations by use of Materia Ver. 3.0 were performed on Sun Sparc 10. The program was purchased from Teijin System Technology Ltd.
  • 47
    • 0013502821 scopus 로고    scopus 로고
    • note
    • 3 in the presence of 1-(t-butyldimethylsiloxy)-1-phenylethene was attempted according to Ref. 14. However, the addition product 17 was not obtained at all, and a chlorinated product 41 was obtained in 33% yield (Chart 1).
  • 48
    • 0001765247 scopus 로고
    • H-y He, D. J. Faulkner, J. S. Shumsky, K. Hong, and J. Clardy, J. Org. Chem., 54, 2511 (1989). 3-Isopropyl-6-isothiocyanato-6, 10-dimethylbicyclo[5.3.0]dec-2-ene is the correct IUPAC nomenclature for this natural product, but 10-isothiocyanatoguaia-6-ene, which was used in the original paper, was employed in this paper for convenience.
    • (1989) J. Org. Chem. , vol.54 , pp. 2511
    • He, H.-Y.1    Faulkner, D.J.2    Shumsky, J.S.3    Hong, K.4    Clardy, J.5
  • 56
    • 0030131103 scopus 로고    scopus 로고
    • For reviews on marine natural products, see: b) D. J. Faulkner, Nat. Prod. Rep., 13, 75 (1996); 14, 259 (1997); 15, 113 (1998).
    • (1996) Nat. Prod. Rep. , vol.13 , pp. 75
    • Faulkner, D.J.1
  • 57
    • 0030841236 scopus 로고    scopus 로고
    • For reviews on marine natural products, see: b) D. J. Faulkner, Nat. Prod. Rep., 13, 75 (1996); 14, 259 (1997); 15, 113 (1998).
    • (1997) Nat. Prod. Rep. , vol.14 , pp. 259
  • 58
    • 0032054664 scopus 로고    scopus 로고
    • For reviews on marine natural products, see: b) D. J. Faulkner, Nat. Prod. Rep., 13, 75 (1996); 14, 259 (1997); 15, 113 (1998).
    • (1998) Nat. Prod. Rep. , vol.15 , pp. 113
  • 59
    • 85023313060 scopus 로고    scopus 로고
    • For some examples of the synthesis of sesquiterpene isothiocyanates of marine origin, see; a) D. J. Hart and C-S. Lai, Synlett, 1989, 49;
    • Synlett , vol.1989 , pp. 49
    • Hart, D.J.1    Lai, C.-S.2
  • 65
    • 0013468817 scopus 로고    scopus 로고
    • note
    • The stereochemistry of the hydroxy group was deduced from the coupling constant (J = 11.6 Hz) of the proton on C-2.
  • 69
    • 0000679590 scopus 로고
    • Reduction of saturated alcohols and amines to alkanes
    • ed by B. M. Trost, Pergamon Press, New York
    • d) S. W. McCombie, "Reduction of Saturated Alcohols and Amines to Alkanes," in "Comprehensive Organic Synthesis," ed by B. M. Trost, Pergamon Press, New York (1991), Vol. 8, p. 811.
    • (1991) Comprehensive Organic Synthesis , vol.8 , pp. 811
    • McCombie, S.W.1
  • 70
    • 0013502823 scopus 로고    scopus 로고
    • note
    • We have not rigorously established the stereochemistry of the addition reaction at this stage. However, the result of the following reductive olefination reaction strongly supported the stereochemistry as shown in 30.
  • 76
    • 0013469108 scopus 로고    scopus 로고
    • note
    • -1) spectra for thiocyano group.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.