메뉴 건너뛰기




Volumn 27, Issue 19, 2013, Pages 1749-1756

A concise total synthesis of the natural carbazole clauraila A

Author keywords

1 methoxycarbazoles; 4,5 dimethylene 2 oxazolidinone dienes; clauraila A; CZH bond activation; Pd(II) cyclisation

Indexed keywords

ACROLEIN; ALKADIENE; AMINE; CARBAZOLE DERIVATIVE; CLAURAILA A; NATURAL PRODUCT; PALLADIUM; UNCLASSIFIED DRUG;

EID: 84887607225     PISSN: 14786419     EISSN: 14786427     Source Type: Journal    
DOI: 10.1080/14786419.2012.751599     Document Type: Article
Times cited : (9)

References (29)
  • 1
    • 84855712324 scopus 로고    scopus 로고
    • Synthesis of pyrrole and carbazole alkaloids
    • Bauer, I., & Knölker, H.-J. (2012). Synthesis of pyrrole and carbazole alkaloids. Topics in Current Chemistry, 309, 203-254.
    • (2012) Topics in Current Chemistry , vol.309 , pp. 203-254
    • Bauer, I.1    Knölker, H.-J.2
  • 2
    • 79952449637 scopus 로고    scopus 로고
    • Total synthesis of the natural carbazoles glycozolicine, mukoline, and mukolidine, starting from 4,5-dimethyleneoxazolidin-2-ones
    • Bautista, R., Bernal, P., Montiel, L. E., Delgado, F., & Tamariz, J. (2011). Total synthesis of the natural carbazoles glycozolicine, mukoline, and mukolidine, starting from 4,5-dimethyleneoxazolidin-2-ones. Synthesis, 929-933.
    • (2011) Synthesis , pp. 929-933
    • Bautista, R.1    Bernal, P.2    Montiel, L.E.3    Delgado, F.4    Tamariz, J.5
  • 3
    • 33845585332 scopus 로고    scopus 로고
    • N-H Carbazole synthesis from 2-chloroanilines via consecutive-amination and CZH activation
    • Bedford, R. B., & Betham, M. (2006). N-H Carbazole synthesis from 2-chloroanilines via consecutive-amination and CZH activation. Journal of Organic Chemistry, 71, 9403-9410.
    • (2006) Journal of Organic Chemistry , vol.71 , pp. 9403-9410
    • Bedford, R.B.1    Betham, M.2
  • 4
    • 7644223178 scopus 로고    scopus 로고
    • Total synthesis of the natural carbazoles murrayanine and murrayafoline A, based on the regioselective Diels-Alder addition of exo-2-oxazolidinone dienes
    • Benavides, A., Peralta, J., Delgado, F., & Tamariz, J. (2004). Total synthesis of the natural carbazoles murrayanine and murrayafoline A, based on the regioselective Diels-Alder addition of exo-2-oxazolidinone dienes. Synthesis, 2499-2504.
    • (2004) Synthesis , pp. 2499-2504
    • Benavides, A.1    Peralta, J.2    Delgado, F.3    Tamariz, J.4
  • 5
    • 34447539978 scopus 로고    scopus 로고
    • Exo-2-Oxazolidinone dienes in the total synthesis of the natural carbazoles 6-methoxymurrayanine and clausenine
    • Bernal, P., Benavides, A., Bautista, R., & Tamariz, J. (2007). exo-2-Oxazolidinone dienes in the total synthesis of the natural carbazoles 6-methoxymurrayanine and clausenine. Synthesis, 1943-1948.
    • (2007) Synthesis , pp. 1943-1948
    • Bernal, P.1    Benavides, A.2    Bautista, R.3    Tamariz, J.4
  • 6
    • 34548402881 scopus 로고    scopus 로고
    • Total synthesis of murrayanine involving 4,5-dimethyleneoxazolidin-2-ones and a palladium(0)-catalyzed diaryl insertion
    • Bernal, P., & Tamariz, J. (2007). Total synthesis of murrayanine involving 4,5-dimethyleneoxazolidin-2-ones and a palladium(0)-catalyzed diaryl insertion. Helvetica Chimica Acta, 90, 1449-1454.
    • (2007) Helvetica Chimica Acta , vol.90 , pp. 1449-1454
    • Bernal, P.1    Tamariz, J.2
  • 7
    • 33644905281 scopus 로고    scopus 로고
    • Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules
    • Campeau, L.-C., & Fagnou, K. (2006). Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules. Chemical Communications, 1253-1264.
    • (2006) Chemical Communications , pp. 1253-1264
    • Campeau, L.-C.1    Fagnou, K.2
  • 11
    • 24644485154 scopus 로고    scopus 로고
    • Occurrence, biological activity, and convergent organometallic synthesis of carbazole alkaloids
    • Knölker, H.-J. (2005). Occurrence, biological activity, and convergent organometallic synthesis of carbazole alkaloids. Topics in Current Chemistry, 244, 115-148.
    • (2005) Topics in Current Chemistry , vol.244 , pp. 115-148
    • Knölker, H.-J.1
  • 12
    • 61849122485 scopus 로고    scopus 로고
    • Synthesis of biologically active carbazole alkaloids using selective transition-metal-catalyzed coupling reactions
    • Knölker, H.-J. (2009). Synthesis of biologically active carbazole alkaloids using selective transition-metal-catalyzed coupling reactions. Chemical Letters, 38, 8-13.
    • (2009) Chemical Letters , vol.38 , pp. 8-13
    • Knölker, H.-J.1
  • 13
    • 33748597689 scopus 로고    scopus 로고
    • Palladium-catalyzed total synthesis of the antibiotic carbazole alkaloids carbazomycin G and H
    • Knölker, H.-J., & Fröhner, W. (1998). Palladium-catalyzed total synthesis of the antibiotic carbazole alkaloids carbazomycin G and H. Journal of the Chemical Society, Perkin Transactions 1, 173-175.
    • (1998) Journal of the Chemical Society, Perkin Transactions , vol.1 , pp. 173-175
    • Knölker, H.-J.1    Fröhner, W.2
  • 14
    • 0036199694 scopus 로고    scopus 로고
    • Indoloquinones, Part 7. Total synthesis of the potent lipid peroxidation inhibitor carbazoquinocin C by an intramolecular palladium-catalyzed oxidative coupling of an anilino-1,4-benzoquinone
    • Knölker, H.-J., Fröhner, W., & Reddy, K. R. (2002). Indoloquinones, Part 7. Total synthesis of the potent lipid peroxidation inhibitor carbazoquinocin C by an intramolecular palladium-catalyzed oxidative coupling of an anilino-1,4-benzoquinone. Synthesis, 557-564.
    • (2002) Synthesis , pp. 557-564
    • Knölker, H.-J.1    Fröhner, W.2    Reddy, K.R.3
  • 15
    • 3843065849 scopus 로고    scopus 로고
    • First total synthesis of the neuronal cell protecting carbazole alkaloid carbazomadurin A by sequential transition metal-catalyzed reactions
    • Knölker, H.-J., & Knöll, J. (2003). First total synthesis of the neuronal cell protecting carbazole alkaloid carbazomadurin A by sequential transition metal-catalyzed reactions. Chemical Communications, 1170-1171.
    • (2003) Chemical Communications , pp. 1170-1171
    • Knölker, H.-J.1    Knöll, J.2
  • 16
    • 0028136733 scopus 로고
    • Palladium-promoted synthesis of hydroxyl-substituted 5-cyano-5H-benzo[b] carbazole-6,11-diones
    • Knölker, H.-J., & O'Sullivan, N. (1994). Palladium-promoted synthesis of hydroxyl-substituted 5-cyano-5H-benzo[b] carbazole-6,11-diones. Tetrahedron, 50, 10893-10908.
    • (1994) Tetrahedron , vol.50 , pp. 10893-10908
    • Knölker, H.-J.1    O'sullivan, N.2
  • 17
    • 0036826933 scopus 로고    scopus 로고
    • Isolation and synthesis of biologically active carbazole alkaloids
    • Knölker, H.-J., & Reddy, K. R. (2002). Isolation and synthesis of biologically active carbazole alkaloids. Chemical Reviews, 102, 4303-4427.
    • (2002) Chemical Reviews , vol.102 , pp. 4303-4427
    • Knölker, H.-J.1    Reddy, K.R.2
  • 18
    • 0038372599 scopus 로고    scopus 로고
    • Indoloquinones, Part 8. Palladium(II)-catalyzed total synthesis of murrayaquinone A, koeniginequinone A, and koeniginequinone B
    • Knölker, H.-J., & Reddy, K. R. (2003). Indoloquinones, Part 8. Palladium(II)-catalyzed total synthesis of murrayaquinone A, koeniginequinone A, and koeniginequinone B. Heterocycles, 60, 1049-1052.
    • (2003) Heterocycles , vol.60 , pp. 1049-1052
    • Knölker, H.-J.1    Reddy, K.R.2
  • 19
    • 44949230366 scopus 로고    scopus 로고
    • Chemistry and biology of carbazole alkaloids
    • In G. A. Cordell (Ed. ) Amsterdam: Academic Press
    • Knölker, H.-J., & Reddy, K. R. (2008). Chemistry and biology of carbazole alkaloids. In G. A. Cordell (Ed. ), The alkaloids chemistry and biology (vol. 65). Amsterdam: Academic Press.
    • (2008) The Alkaloids Chemistry and Biology , vol.65
    • Knölker, H.-J.1    Reddy, K.R.2
  • 20
    • 33747876110 scopus 로고    scopus 로고
    • First total synthesis of the 7-oxygenated carbazole alkaloid clauszoline-K, 3-formyl-7-hydroxycarbazole, clausine M, clausine N and the anti-HIV active siamenol using a highly efficient palladium-catalyzed approach
    • Krahl, M. P., Jäger, A., Krause, T., & Knölker, H.-J. (2006). First total synthesis of the 7-oxygenated carbazole alkaloid clauszoline-K, 3-formyl-7-hydroxycarbazole, clausine M, clausine N and the anti-HIV active siamenol using a highly efficient palladium-catalyzed approach. Organic & Biomolecular Chemistry, 4, 3215-3219.
    • (2006) Organic & Biomolecular Chemistry , vol.4 , pp. 3215-3219
    • Krahl, M.P.1    Jäger, A.2    Krause, T.3    Knölker, H.-J.4
  • 21
    • 26844501399 scopus 로고    scopus 로고
    • New synthesis of carbazoles from novel exo-2-oxazolidinone dienes
    • Mandal, A. B., Delgado, F., & Tamariz, J. (1998). New synthesis of carbazoles from novel exo-2-oxazolidinone dienes. Synlett, 87-89.
    • (1998) Synlett , pp. 87-89
    • Mandal, A.B.1    Delgado, F.2    Tamariz, J.3
  • 22
  • 23
    • 84860624351 scopus 로고    scopus 로고
    • Occurrence, biogenesis, and synthesis of biologically active carbazole alkaloids
    • Schmidt, A. W., Reddy, K. R., & Knölker, H.-J. (2012). Occurrence, biogenesis, and synthesis of biologically active carbazole alkaloids. Chemical Reviews, 112, 3193-3328.
    • (2012) Chemical Reviews , vol.112 , pp. 3193-3328
    • Schmidt, A.W.1    Reddy, K.R.2    Knölker, H.-J.3
  • 24
    • 70449379418 scopus 로고    scopus 로고
    • Transition metals in organic synthesis, Part 91: Palladium-catalyzed approach to 2,6-dioxygenated carbazole alkaloids-First total synthesis of the phytoalexin carbalexin C
    • Schmidt, M., & Knölker, H.-J. (2009). Transition metals in organic synthesis, Part 91: Palladium-catalyzed approach to 2,6-dioxygenated carbazole alkaloids-First total synthesis of the phytoalexin carbalexin C. Synlett, 2421-2424.
    • (2009) Synlett , pp. 2421-2424
    • Schmidt, M.1    Knölker, H.-J.2
  • 25
    • 79952293839 scopus 로고    scopus 로고
    • Claurailas A-D, cytotoxic carbazole alkaloids from the roots of Clausena harmandiana
    • Songsiang, U., Thongthoom, T., Boonyarat, C., & Yenjai, C. (2011). Claurailas A-D, cytotoxic carbazole alkaloids from the roots of Clausena harmandiana. Journal of Natural Products, 74, 208-212.
    • (2011) Journal of Natural Products , vol.74 , pp. 208-212
    • Songsiang, U.1    Thongthoom, T.2    Boonyarat, C.3    Yenjai, C.4
  • 26
    • 70349227133 scopus 로고    scopus 로고
    • Acid-free synthesis of carbazoles and carbazolequinones by intramolecular Pd-catalyzed, microwave-assisted oxidative biaryl coupling reactions-efficient syntheses of murrayafoline A, 2-methoxy-3-methylcarbazole, and glycozolidine
    • Sridharan, V., Mart?́n, M. A., & Menéndez, J. C. (2009). Acid-free synthesis of carbazoles and carbazolequinones by intramolecular Pd-catalyzed, microwave-assisted oxidative biaryl coupling reactions-efficient syntheses of murrayafoline A, 2-methoxy-3-methylcarbazole, and glycozolidine. European Journal of Organic Chemistry, 4614-4621.
    • (2009) European Journal of Organic Chemistry , pp. 4614-4621
    • Sridharan, V.1    Mart́n, M.A.2    Menéndez, J.C.3
  • 27
    • 82455192845 scopus 로고    scopus 로고
    • Lewis acid-promoted synthesis of unsymmetrical and highly functionalized carbazoles and dibenzofurans from biaryl triazenes: Application for the total synthesis of clausine C, clausine R, and clauraila A
    • Yang, W., Zhou, J., Wang, B., & Ren, H. (2011). Lewis acid-promoted synthesis of unsymmetrical and highly functionalized carbazoles and dibenzofurans from biaryl triazenes: Application for the total synthesis of clausine C, clausine R, and clauraila A. Chemistry a European Journal, 17, 13665-13669.
    • (2011) Chemistry A European Journal , vol.17 , pp. 13665-13669
    • Yang, W.1    Zhou, J.2    Wang, B.3    Ren, H.4
  • 29
    • 0036470739 scopus 로고    scopus 로고
    • A concise synthesis of the natural carbazole mukonine
    • Zempoalteca, A., & Tamariz, J. (2002). A concise synthesis of the natural carbazole mukonine. Heterocycles, 57, 259-267.
    • (2002) Heterocycles , vol.57 , pp. 259-267
    • Zempoalteca, A.1    Tamariz, J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.