메뉴 건너뛰기




Volumn 12, Issue 5-6, 2000, Pages 374-377

Efficient asymmetric synthesis of α-alkylated 1,4-cyclohexanedione derivatives, important chiral building blocks in the synthesis of natural products

Author keywords

Asymmetric synthesis; Hydrazone cleavage; Ketone reduction; Mono protected cyclohexanediones; SAMP hydrazones; alkylation

Indexed keywords

1,4 BENZOQUINONE; HYDRAZONE DERIVATIVE; NATURAL PRODUCT;

EID: 0343091512     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1520-636x(2000)12:5/6<374::aid-chir13>3.0.co;2-g     Document Type: Article
Times cited : (16)

References (23)
  • 1
    • 0006091236 scopus 로고
    • An annulation method to fused bicyclic systems containing an allylic, angular hydroxyl group
    • Piers E, Marais PC. An annulation method to fused bicyclic systems containing an allylic, angular hydroxyl group. Tetrahedron Lett 1988; 29:4053-4056.
    • (1988) Tetrahedron Lett , vol.29 , pp. 4053-4056
    • Piers, E.1    Marais, P.C.2
  • 2
    • 0026742502 scopus 로고
    • A bridgehead enone approach to huperzine A
    • Kraus GA, Hansen J, Vines D. A bridgehead enone approach to huperzine A. Synth Comm 1992;22:2625-2634.
    • (1992) Synth Comm , vol.22 , pp. 2625-2634
    • Kraus, G.A.1    Hansen, J.2    Vines, D.3
  • 3
    • 0026101275 scopus 로고
    • Synthesis of (+)- and (-)- and (±)-7′-hydroxyabscisic acid
    • Nelson LAK, Shaw AC, Abrams SR. Synthesis of (+)-and (-)-and (±)-7′-hydroxyabscisic acid. Tetrahedron 1991;47:3259-3270.
    • (1991) Tetrahedron , vol.47 , pp. 3259-3270
    • Nelson, L.A.K.1    Shaw, A.C.2    Abrams, S.R.3
  • 4
    • 0000852344 scopus 로고
    • Stereoselective synthesis of cis-decalins via Diels-Alder and double Michael addition of substituted Nazarov reagents
    • Lavallée J-F, Spino C, Ruel R, Hogan KT, Deslongchamps P. Stereoselective synthesis of cis-decalins via Diels-Alder and double Michael addition of substituted Nazarov reagents. Can J Chem 1992;70:1406-1426.
    • (1992) Can J Chem , vol.70 , pp. 1406-1426
    • Lavallée, J.-F.1    Spino, C.2    Ruel, R.3    Hogan, K.T.4    Deslongchamps, P.5
  • 5
    • 84985687814 scopus 로고
    • Acid-catalyzed and Lewis acid-promoted synthesis of 6-hydroxy-bicyclo[4.3.0]nonan-3-ones
    • Schinzer D, Ruppelt M. Acid-catalyzed and Lewis acid-promoted synthesis of 6-hydroxy-bicyclo[4.3.0]nonan-3-ones. Chem Ber 1991;124: 247-248.
    • (1991) Chem Ber , vol.124 , pp. 247-248
    • Schinzer, D.1    Ruppelt, M.2
  • 6
    • 33751385931 scopus 로고
    • Introduction of the 2-(phenylthio)ethyl, 2-(phenylsulfinyl)ethyl and 2,2-bis(phenylthio)ethyl substituents into cyclic ketones
    • Montgomery J, Overman LE. Introduction of the 2-(phenylthio)ethyl, 2-(phenylsulfinyl)ethyl and 2,2-bis(phenylthio)ethyl substituents into cyclic ketones. J Org Chem 1993;58:6476-6479.
    • (1993) J Org Chem , vol.58 , pp. 6476-6479
    • Montgomery, J.1    Overman, L.E.2
  • 7
    • 4243690056 scopus 로고
    • Annulations leading to diene systems. Total synthesis of the diterpenoid (±)-(14s)-Dolasta-1(15),7,9-trien-14-ol
    • Piers E, Friesen RW. Annulations leading to diene systems. Total synthesis of the diterpenoid (±)-(14S)-Dolasta-1(15),7,9-trien-14-ol. J Chem Soc 1986;5:3405-3406.
    • (1986) J Chem Soc , vol.5 , pp. 3405-3406
    • Piers, E.1    Friesen, R.W.2
  • 8
    • 0028795518 scopus 로고
    • Identification and synthesis of sordidin, a male pheromone emitted by cosmopolites sordidus
    • Beauhaire J, Ducrot P-H, Malosse C, Rochat D. Identification and synthesis of sordidin, a male pheromone emitted by cosmopolites sordidus. Tetrahedron Lett 1995;36:1043-1046.
    • (1995) Tetrahedron Lett , vol.36 , pp. 1043-1046
    • Beauhaire, J.1    Ducrot, P.-H.2    Malosse, C.3    Rochat, D.4
  • 10
    • 0029017569 scopus 로고
    • Short and efficient synthesis of (R)-4-hydroxy-4-methylcyclohexenone
    • Bueno AB, Carreño MC, García Ruano JL. Short and efficient synthesis of (R)-4-hydroxy-4-methylcyclohexenone. Tetrahedron Lett 1995;36: 3737-3740.
    • (1995) Tetrahedron Lett , vol.36 , pp. 3737-3740
    • Bueno, A.B.1    Carreño, M.C.2    García Ruano, J.L.3
  • 12
    • 0000058030 scopus 로고
    • Efficient synthesis of the natural enantiomer of sporogen AO 1 (13-desoxyphomenone). A sporogenic sesquiterpene from Aspergillus oryzae
    • and literature citied therein
    • Kitahara T, Kurata H, Mori K. Efficient synthesis of the natural enantiomer of sporogen AO 1 (13-desoxyphomenone). A sporogenic sesquiterpene from Aspergillus oryzae. Tetrahedron 1988;44:4339-4349, and literature citied therein.
    • (1988) Tetrahedron , vol.44 , pp. 4339-4349
    • Kitahara, T.1    Kurata, H.2    Mori, K.3
  • 13
    • 85047671779 scopus 로고
    • Enantioselective total synthetic route to (+)-aphidicolin
    • and literature cited therein
    • Toyota M, Nishikawa Y, Fukumoto K. Enantioselective total synthetic route to (+)-aphidicolin. Tetrahedron Lett 1995;36:5379-5382, and literature cited therein.
    • (1995) Tetrahedron Lett , vol.36 , pp. 5379-5382
    • Toyota, M.1    Nishikawa, Y.2    Fukumoto, K.3
  • 14
    • 0026671464 scopus 로고
    • New mild methodology for the synthesis of α-phenylthio and α-phenylseleno ketones
    • Magnus P, Rigollier P. New mild methodology for the synthesis of α-phenylthio and α-phenylseleno ketones. Tetrahedron Lett 1992;33: 6111-6114.
    • (1992) Tetrahedron Lett , vol.33 , pp. 6111-6114
    • Magnus, P.1    Rigollier, P.2
  • 15
    • 0027967831 scopus 로고
    • A new cyclopentenone annulation method
    • Piers E, Cook KL, Rogers C. A new cyclopentenone annulation method. Tetrahedron Lett 1994;35:8873-8876.
    • (1994) Tetrahedron Lett , vol.35 , pp. 8873-8876
    • Piers, E.1    Cook, K.L.2    Rogers, C.3
  • 16
    • 0002754795 scopus 로고    scopus 로고
    • Stereoselective conjugate addition directed by an enantiomerically pure ketal. Preparation of the cyclohexanone fragment of N-methylwelwitindolinone C isothiocyanate
    • Konopelski JP, Deng H, Schiemann K, Keane JM, Olmstaed MM. Stereoselective conjugate addition directed by an enantiomerically pure ketal. Preparation of the cyclohexanone fragment of N-methylwelwitindolinone C isothiocyanate. Synlett 1998;1105-1107.
    • (1998) Synlett , pp. 1105-1107
    • Konopelski, J.P.1    Deng, H.2    Schiemann, K.3    Keane, J.M.4    Olmstaed, M.M.5
  • 17
    • 37049085898 scopus 로고
    • Michael reaction of functionalized chiral cyclanone imines. Enantioselective synthesis of C2-symmetric cis-(1R,6R)-1,6-dimethylbicyclo[4.4.0]decane-3,8-dione
    • Pfau M, Jabin I, Revial G. Michael reaction of functionalized chiral cyclanone imines. Enantioselective synthesis of C2-symmetric cis-(1R,6R)-1,6-dimethylbicyclo[4.4.0]decane-3,8-dione. J Chem Soc Perkin Trans 1 1993;17:1935-1936.
    • (1993) J Chem Soc Perkin Trans 1 , vol.17 , pp. 1935-1936
    • Pfau, M.1    Jabin, I.2    Revial, G.3
  • 18
    • 84982456512 scopus 로고
    • Asymmetric synthesis via metalated chiral hydrazones. Enantioselective alkylation of cyclic ketones und aldehydes
    • Enders D, Eichenauer H. Asymmetric synthesis via metalated chiral hydrazones. Enantioselective alkylation of cyclic ketones und aldehydes. Chem Ber 1979;112:2933-2960.
    • (1979) Chem Ber , vol.112 , pp. 2933-2960
    • Enders, D.1    Eichenauer, H.2
  • 19
    • 0002853558 scopus 로고    scopus 로고
    • Mild, racemation free cleavage of ketone SAMP hydrazones with oxalic acid - Recycling of the chiral auxiliary
    • Enders D, Hundertmark T, Lazny R. Mild, racemation free cleavage of ketone SAMP hydrazones with oxalic acid - recycling of the chiral auxiliary. Synlett 1998;721-722.
    • (1998) Synlett , pp. 721-722
    • Enders, D.1    Hundertmark, T.2    Lazny, R.3
  • 20
    • 0032980696 scopus 로고    scopus 로고
    • Copper(II) chloride mediated hydrolysis of α-alkylated ketone SAMP-hydrazones
    • Enders D, Hundertmark T, Lazny R. Copper(II) chloride mediated hydrolysis of α-alkylated ketone SAMP-hydrazones. Synth Commun 1999;29:27-33.
    • (1999) Synth Commun , vol.29 , pp. 27-33
    • Enders, D.1    Hundertmark, T.2    Lazny, R.3
  • 21
    • 0010640653 scopus 로고
    • α-Methoxy-α-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines
    • Dale JA, Dull DL, Mosher HS. α-Methoxy-α-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines. J Org Chem 1969;34:2543-2549.
    • (1969) J Org Chem , vol.34 , pp. 2543-2549
    • Dale, J.A.1    Dull, D.L.2    Mosher, H.S.3
  • 22
    • 0002002903 scopus 로고
    • Facile conversion of N,N-dimethylhydrazones to carbonyl compounds by cupric ion-catalyzed hydrolysis
    • Corey EJ, Knapp S. Facile conversion of N,N-dimethylhydrazones to carbonyl compounds by cupric ion-catalyzed hydrolysis. Tetrahedron Lett 1976;3667-3668.
    • (1976) Tetrahedron Lett , pp. 3667-3668
    • Corey, E.J.1    Knapp, S.2
  • 23
    • 0000170052 scopus 로고
    • The use of solvating agents for nuclear magnetic resonance determination of enantiomeric purity and absolute configuration of lactones. Consequences of three-point interactions
    • Pirkle WH, Sikkenga DL. The use of solvating agents for nuclear magnetic resonance determination of enantiomeric purity and absolute configuration of lactones. Consequences of three-point interactions. J Org Chem 1977;42:1370-1374.
    • (1977) J Org Chem , vol.42 , pp. 1370-1374
    • Pirkle, W.H.1    Sikkenga, D.L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.