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Volumn 63, Issue 26, 1998, Pages 9782-9793

Total synthesis of (-)-macrocarpal C. Stereoselective coupling reaction with a novel hexasubstituted benzene Cr(CO)3 complex as a biomimetic chiral benzyl cation equivalent

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; MACROCARPAL C; UNCLASSIFIED DRUG;

EID: 0032567425     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981413+     Document Type: Article
Times cited : (31)

References (94)
  • 1
    • 0030041261 scopus 로고    scopus 로고
    • For a review of bioactive acylphloroglucinol derivatives from Eucalyptus species, see: Ghisalberti, E. L. Phytochemistry 1996, 42, 7.
    • (1996) Phytochemistry , vol.42 , pp. 7
    • Ghisalberti, E.L.1
  • 10
    • 20644469294 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra of macrocarpals C 3 and G 4 were measured in different solvents, which made comparison difficult. In ref 1, it has been considered that these were diastereomers due to difference between their physicochemical properties.
  • 21
    • 0003662244 scopus 로고
    • When the corresponding benzyl acetate was used for the coupling reaction, none of the desired product was obtained. For examples for the coupling reaction of benzyl acetates with silylenol ethers, see: Reetz, M. T.; Hüttenhain, S.; Hübner, F. Synth. Commun. 1981,11, 217.
    • (1981) Synth. Commun. , vol.11 , pp. 217
    • Reetz, M.T.1    Hüttenhain, S.2    Hübner, F.3
  • 25
    • 0010849445 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, Chapter 8.
    • 3 complexes, see: Morris, M. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 5, Chapter 8.
    • (1995) Comprehensive Organometallic Chemistry II , vol.5
    • Morris, M.J.1
  • 26
    • 0003625966 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, Chapter 9.3.
    • Davies, S. G.; McCarthy, T. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 9.3.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12
    • Davies, S.G.1    McCarthy, T.D.2
  • 34
    • 33847520026 scopus 로고    scopus 로고
    • The reaction should be carried out at 120 ± 5 °C (bath temperature) since 19 decomposes (decomplexes) at 136 °C.
    • The reaction should be carried out at 120 ± 5 °C (bath temperature) since 19 decomposes (decomplexes) at 136 °C.
  • 39
    • 33847501725 scopus 로고    scopus 로고
    • Direct Cr-complexation of the antecedent diester 16 was failed under various conditions.
    • Direct Cr-complexation of the antecedent diester 16 was failed under various conditions.
  • 40
    • 20644472091 scopus 로고    scopus 로고
    • note
    • 22
  • 50
    • 33847491562 scopus 로고    scopus 로고
    • 27
    • 27
  • 69
    • 49049128445 scopus 로고
    • For a review on Barton deoxygenation, see: Hartwig, W. Tetrahedron 1983, 39, 2609.
    • (1983) Tetrahedron , vol.39 , pp. 2609
    • Hartwig, W.1
  • 71
    • 85038134535 scopus 로고
    • Trost, B. M., Eds.; Pergamon: New York, Chapter 4.2.
    • McCombie, S. W. In Comprehensive Organic Synthesis; Trost, B. M., Eds.; Pergamon: New York, 1991; Vol. 8, Chapter 4.2.
    • (1991) Comprehensive Organic Synthesis , vol.8
    • McCombie, S.W.1
  • 73
    • 20644436097 scopus 로고    scopus 로고
    • note
    • It appears that the formation of the byproduct 27 was attributed to more reactive l,l'-carbonyldiimidazole as contamination of 1,1′-thiocarbonyldiimidazole used in a large excess. In fact, treatment of 25 with 1.1′-carbonyldiimidazole under the same condition afforded only 27 (83% yield).
  • 74
    • 20644451075 scopus 로고    scopus 로고
    • note
    • The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre (CCDC 182/601). The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
  • 79
    • 33847510984 scopus 로고    scopus 로고
    • To remove the excess of reagents, we operated the oxidative workup before isolation.
    • To remove the excess of reagents, we operated the oxidative workup before isolation.
  • 88
    • 33847526746 scopus 로고    scopus 로고
    • 3CN.
    • 3CN.
  • 89
    • 33847510320 scopus 로고    scopus 로고
    • Lithiump-thiocresolate is conveniently prepared in quantitative yield fromp-thiocresol and n-BuLi in toluene at 0 °C. This salt can be stored at room temperature in a desiccator for months.
    • Lithiump-thiocresolate is conveniently prepared in quantitative yield fromp-thiocresol and n-BuLi in toluene at 0 °C. This salt can be stored at room temperature in a desiccator for months.
  • 94
    • 33847524457 scopus 로고    scopus 로고
    • Nishizawa, M., a personal letter on April 15
    • Nishizawa, M., a personal letter on April 15, 1997.
    • (1997)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.