메뉴 건너뛰기




Volumn 14, Issue 11, 2010, Pages 1139-1152

The pauson-khand reaction in the synthesis of pharmacologically active compounds

Author keywords

[No Author keywords available]

Indexed keywords

CARBON MONOXIDE;

EID: 77954897320     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527210791317085     Document Type: Article
Times cited : (16)

References (47)
  • 1
    • 37049121676 scopus 로고
    • Organocobalt Complexes. Part I. Arene Complexes Derived From dodecacarbonyltetracobalt
    • Khand, I.U.; Knox, G.R.; Pauson, P.L.; Watts, W.E. Organocobalt complexes. Part I. Arene complexes derived from dodecacarbonyltetracobalt. J. Chem. Soc. Perkin Trans. 1 1973, 975-977
    • (1973) J. Chem. Soc. Perkin Trans. 1 , pp. 975-977
    • Khand, I.U.1    Knox, G.R.2    Pauson, P.L.3    Watts, W.E.4
  • 3
    • 0003064834 scopus 로고
    • Organocobalt complexes. Part VIII. Specificity of the cyclopentenone synthesis from acetylenehexacarbonyldicobalt complexes and norbornene derivatives
    • Khand, I.U.; Pauson, P.L. Organocobalt complexes. Part VIII. Specificity of the cyclopentenone synthesis from acetylenehexacarbonyldicobalt complexes and norbornene derivatives. J. Chem. Soc., Perkin Trans. 1 1976, 30-32.
    • (1976) J. Chem. Soc., Perkin Trans , vol.1 , pp. 30-32
    • Khand, I.U.1    Pauson, P.L.2
  • 4
    • 0025046680 scopus 로고
    • N-oxide promoted PausonKhand cyclizations at room temperature
    • Shambayati, S.; Crowe, W.E.; Schreiber, S.L. N-oxide promoted PausonKhand cyclizations at room temperature. Tetrahedron Lett. 1990, 31, 5289-5292.
    • (1990) Tetrahedron Lett , vol.31 , pp. 5289-5292
    • Shambayati, S.1    Crowe, W.E.2    Schreiber, S.L.3
  • 5
    • 0000134751 scopus 로고
    • The Khand reaction: A convenient and general route to a wide range of cyclopentenone derivatives
    • Pauson, P.L. The Khand reaction: A convenient and general route to a wide range of cyclopentenone derivatives. Tetrahedron 1985, 41, 5855-5860.
    • (1985) Tetrahedron , vol.41 , pp. 5855-5860
    • Pauson, P.L.1
  • 6
    • 0034686072 scopus 로고    scopus 로고
    • Recent advances in the Pauson-Khand reaction and related [2+2+1] cycloadditions
    • Brummond, K.M.; Kent, J.J. Recent advances in the Pauson-Khand reaction and related [2+2+1] cycloadditions. Tetrahedron 2000, 56, 3263-3283
    • (2000) Tetrahedron , vol.56 , pp. 3263-3283
    • Brummond, K.M.1    Kent, J.J.2
  • 7
    • 0038665161 scopus 로고    scopus 로고
    • The Pauson-Khand reaction: The catalytic age is here
    • Gibson, S.E.; Stevenazzi, A. The Pauson-Khand reaction: the catalytic age is here! Angew. Chem. Int. Ed. 2003, 42, 1800-1810
    • (2003) Angew. Chem. Int. Ed , vol.42 , pp. 1800-1810
    • Gibson, S.E.1    Stevenazzi, A.2
  • 9
    • 18844403627 scopus 로고    scopus 로고
    • The intermolecular Pauson-Khand reaction
    • Gibson, S.E.; Mainolfi, N. The intermolecular Pauson-Khand reaction. Angew. Chem. Int. Ed. 2005, 44, 3022-3037
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 3022-3037
    • Gibson, S.E.1    Mainolfi, N.2
  • 10
    • 33845245890 scopus 로고    scopus 로고
    • Recent advances in the catalytic Pauson-Khand-type reaction
    • Shibata, T. Recent advances in the catalytic Pauson-Khand-type reaction. Adv. Synth. Catal. 2006, 348, 2328-2336.
    • (2006) Adv. Synth. Catal , vol.348 , pp. 2328-2336
    • Shibata, T.1
  • 11
    • 0039541691 scopus 로고
    • Methylenomycin B: An efficient synthesis from (2-butyne)hexacarbonyldicobalt
    • Billington, D.C.; Pauson, P.L. Methylenomycin B: an efficient synthesis from (2-butyne)hexacarbonyldicobalt. Organometallics 1982, 1, 1560-1561.
    • (1982) Organometallics , vol.1 , pp. 1560-1561
    • Billington, D.C.1    Pauson, P.L.2
  • 12
    • 8344247714 scopus 로고    scopus 로고
    • Vinyl sulfoxides as stereochemical controllers in intermolecular Pauson-Khand reactions: Applications to the enantioselective synthesis of natural cyclopentanoids
    • Rodríguez Rivero, M.; Alonso, I.; Carretero, J.C. Vinyl sulfoxides as stereochemical controllers in intermolecular Pauson-Khand reactions: Applications to the enantioselective synthesis of natural cyclopentanoids. Chem. Eur. J. 2004, 10, 5443-5459.
    • (2004) Chem. Eur. J , vol.10 , pp. 5443-5459
    • Rodríguez Rivero, M.1    Alonso, I.2    Carretero, J.C.3
  • 13
    • 0033165960 scopus 로고    scopus 로고
    • Pauson-Khand reaction of activated olefins
    • Ahmar, M.; Antras, F.; Cazes, B. Pauson-Khand reaction of activated olefins. Tetrahedron Lett. 1999, 40, 5503-5506.
    • (1999) Tetrahedron Lett , vol.40 , pp. 5503-5506
    • Ahmar, M.1    Antras, F.2    Cazes, B.3
  • 16
    • 57049169922 scopus 로고    scopus 로고
    • The conjugate addition-Peterson olefination reaction for the preparation of cross-conjugated-cyclopentenone, PPARligands
    • Iqbal, M.; Duffy, P.; Evans, P.; Cloughley, G.; Allan, B.; Lledo, A.; Verdaguer, X.; Riera, A. The conjugate addition-Peterson olefination reaction for the preparation of cross-conjugated-cyclopentenone, PPARligands. Org.Biomol. Chem. 2008, 6, 4649-4661.
    • (2008) Org.Biomol. Chem , vol.6 , pp. 4649-4661
    • Iqbal, M.1    Duffy, P.2    Evans, P.3    Cloughley, G.4    Allan, B.5    Lledo, A.6    Verdaguer, X.7    Riera, A.8
  • 17
    • 58149163037 scopus 로고    scopus 로고
    • Enantioselective syntheses of carbanucleosides from the Pauson-Khand adduct of trimethylsilylacetylene and norbornadiene
    • Vázquez-Romero, A.; Rodríguez, J.; Lledo, A.; Verdaguer, X.; Riera, A. Enantioselective syntheses of carbanucleosides from the Pauson-Khand adduct of trimethylsilylacetylene and norbornadiene. Org. Lett. 2008, 10, 4509-4512.
    • (2008) Org. Lett , vol.10 , pp. 4509-4512
    • Vázquez-Romero, A.1    Rodríguez, J.2    Lledo, A.3    Verdaguer, X.4    Riera, A.5
  • 19
    • 0041897371 scopus 로고
    • Alkyne-cobalt complexes as prostaglandin synthons. Simple preparations of known intermediates for 1- and 2-series prostaglandin formation and synthesis of (+/-)-11-deoxy- 10,11 -trimethyleneprostaglandin E1 methyl ester
    • 1980, J. Chem. Res. (M)
    • Newton, R.F.; Pauson, P.L.; Taylor, R.G. Alkyne-cobalt complexes as prostaglandin synthons. Simple preparations of known intermediates for 1- and 2-series prostaglandin formation and synthesis of (+/-)-11-deoxy- 10,11 -trimethyleneprostaglandin E1 methyl ester. J. Chem. Res. (S) 1980, 277; J. Chem. Res. (M) 1980, 3501-3522
    • (1980) J. Chem. Res. (S) , vol.277 , pp. 3501-3522
    • Newton, R.F.1    Pauson, P.L.2    Taylor, R.G.3
  • 20
    • 0010924853 scopus 로고
    • Alkyne-cobalt complexes as prostaglandin synthons II. (+/-)-11 Deoxyprostaglandin E Analogues With Furan and Thiophene Rings In the Side-chain
    • 1983, 244 J. Chem. Res. (M)
    • Jaffer, H.J.; Pauson, P.L. Alkyne-cobalt complexes as prostaglandin synthons. II. (+/-)-11- Deoxyprostaglandin E analogues with furan and thiophene rings in the side-chain. J. Chem. Res. (S) 1983, 244 J. Chem. Res. (M) 1983, 2201-2218
    • (1983) J. Chem. Res. (S) , pp. 2201-2218
    • Jaffer, H.J.1    Pauson, P.L.2
  • 21
    • 0007359242 scopus 로고
    • Alkyne-cobalt complexes as prostaglandin synthons. IV. A possible approach via 2- phenylthiocyclopent-2-enone
    • 346 J. Chem. Res. (M)
    • Daalman, L.; Newton, R.F.; Pauson, P.L.; Wadsworth, A. Alkyne-cobalt complexes as prostaglandin synthons. IV. A possible approach via 2- phenylthiocyclopent-2-enone. J. Chem. Res. (S) 1984, 346 J. Chem. Res. (M) 1984, 3150-3164.
    • (1984) J. Chem. Res. (S) , pp. 3150-3164
    • Daalman, L.1    Newton, R.F.2    Pauson, P.L.3    Wadsworth, A.4
  • 22
    • 0016267312 scopus 로고
    • Synthesis of prostaglandins by conjugate addition and alkylation of a directed enolate ion. 11-Deoxy prostaglandins
    • Patterson, J.W.; Fried, J.H. Synthesis of prostaglandins by conjugate addition and alkylation of a directed enolate ion. 11-Deoxy prostaglandins. J. Org. Chem. 1974, 39, 2506-2509
    • (1974) J. Org. Chem , vol.39 , pp. 2506-2509
    • Patterson, J.W.1    Fried, J.H.2
  • 27
    • 0035921090 scopus 로고    scopus 로고
    • A novel synthesis of 9-cis- retinoic acid and tagretin analogues via the Pauson-Khand or Heck reaction
    • Murray, A.; Hansen, J.B.; Christensen, B.V. A novel synthesis of 9-cis- retinoic acid and tagretin analogues via the Pauson-Khand or Heck reaction. Tetrahedron 2001, 57, 7383-7390.
    • (2001) Tetrahedron , vol.57 , pp. 7383-7390
    • Murray, A.1    Hansen, J.B.2    Christensen, B.V.3
  • 28
    • 0000008041 scopus 로고
    • A comparison of (chloromethyl)- and (io- domethyl)zinc cyclopropanation reagents
    • Denmark, S.E.; Edwards, J.P. A comparison of (chloromethyl)- and (io- domethyl)zinc cyclopropanation reagents. J. Org. Chem. 1991, 56, 6974-6981.
    • (1991) J. Org. Chem , vol.56 , pp. 6974-6981
    • Denmark, S.E.1    Edwards, J.P.2
  • 30
    • 0027300216 scopus 로고
    • A total synthesis of (-)--kainic acid by the Pauson-Khand reaction
    • Yoo, S.-E.; Lee, S.-H.; Jeong, N.; Cho, I. A total synthesis of (-)--kainic acid by the Pauson-Khand reaction. Tetrahedron Lett. 1993, 34, 3435-3438.
    • (1993) Tetrahedron Lett , vol.34 , pp. 3435-3438
    • Yoo, S.-E.1    Lee, S.-H.2    Jeong, N.3    Cho, I.4
  • 31
    • 85196230587 scopus 로고
    • Intermediate for synthesis of kainic acid and its production
    • JP 05213871 A
    • Takano, S.; Inomata, K.; Ogasawara, K. Intermediate for synthesis of kainic acid and its production. JP 05213871 A, 1993.
    • (1993)
    • Takano, S.1    Inomata, K.2    Ogasawara, K.3
  • 32
    • 0029978630 scopus 로고    scopus 로고
    • Solid phase synthesis of azabicyclo [4.3.0]nonen-8-one amino acid derivatives via intramolecular Pauson-Khand cyclization
    • Bolton, G.L. Solid phase synthesis of azabicyclo [4.3.0]nonen-8-one amino acid derivatives via intramolecular Pauson-Khand cyclization. Tetrahedron Lett. 1996, 37, 3433-3436
    • (1996) Tetrahedron Lett , vol.37 , pp. 3433-3436
    • Bolton, G.L.1
  • 33
    • 0030987008 scopus 로고    scopus 로고
    • Solid phase synthesis of fused bicyclic amino acid derivatives via in- tramolecular Pauson-Khand cyclization
    • Bolton, G.L.; Hodges, J.C.; Rubin, J.R. Solid phase synthesis of fused bicyclic amino acid derivatives via in- tramolecular Pauson-Khand cyclization: Versatile scaffolds for combinatorial chemistry. Tetrahedron 1997, 53, 6611-6634.
    • (1997) Versatile Scaffolds For Combinatorial Chemistry. Tetrahedron , vol.53 , pp. 6611-6634
    • Bolton, G.L.1    Hodges, J.C.2    Rubin, J.R.3
  • 36
    • 85196228909 scopus 로고    scopus 로고
    • th ACS National Meeting, New Or-leans, U.S., Poster MEDI-291
    • th ACS National Meeting, 2003, New Or-leans, U.S., Poster MEDI-291.
    • (2003)
    • Batra, H.1    Moriarty, R.M.2
  • 37
    • 0026716857 scopus 로고
    • New aza(nor)adamantanes are agonists at the newly identified serotonin 5-HT4 receptor and antagonists at the 5-HT3 re- ceptor. Bioorg. Med
    • Flynn, D.L.; Becker, D.P.; Spangler, D.P.; Nosal, R.; Gullikson, G.W.; Moummi, C.; Yang, D.-C. New aza(nor)adamantanes are agonists at the newly identified serotonin 5-HT4 receptor and antagonists at the 5-HT3 re- ceptor. Bioorg. Med. Chem. Lett. 1992, 2, 1613-1618
    • (1992) Chem. Lett , vol.2 , pp. 1613-1618
    • Flynn, D.L.1    Becker, D.P.2    Spangler, D.P.3    Nosal, R.4    Gullikson, G.W.5    Moummi, C.6    Yang, D.-C.7
  • 38
    • 0027406256 scopus 로고
    • Studies of the solid-phase Pauson-Khand reaction: Selective in- situ enone reduction to 3-azabicyclo [3.3.0]octanones
    • Becker, D.P.; Flynn, D.L. Studies of the solid-phase Pauson-Khand reaction: Selective in- situ enone reduction to 3-azabicyclo [3.3.0]octanones. Tetrahedron Lett. 1993, 34, 2087-2090
    • (1993) Tetrahedron Lett , vol.34 , pp. 2087-2090
    • Becker, D.P.1    Flynn, D.L.2
  • 39
    • 0027157468 scopus 로고
    • Synthesis of N-BOC-3- azabicyclo [3.3.0]octan-7-one via reductive Pauson-Khand cyclization and subsequent conversion to a novel diazatricyclic ring system
    • Becker, D.P.; Flynn, D.L. Synthesis of N-BOC-3- azabicyclo [3.3.0]octan-7-one via reductive Pauson-Khand cyclization and subsequent conversion to a novel diazatricyclic ring system. Tetrahedron 1993, 49, 5047-5054.
    • (1993) Tetrahedron , vol.49 , pp. 5047-5054
    • Becker, D.P.1    Flynn, D.L.2
  • 40
    • 3242727650 scopus 로고
    • Adsorption ef- fects on the efficiency of cobalt-mediated cyclizations of allylpropargyl e- thers into derivatives of 3-oxabicyclo [3.3.0]oct-5-en-7-one
    • Simonyan, S.O.; Smit, W.A.; Gybin, A.S.; Schashkov, A.S.; Mikaelian, G.S.; Tarasov, V.A.; Ibragimov, I.I.; Caple, R.; Froen, D.E. Adsorption ef- fects on the efficiency of cobalt-mediated cyclizations of allylpropargyl e- thers into derivatives of 3-oxabicyclo [3.3.0]oct-5-en-7-one. Tetrahedron Lett. 1986, 27, 1245-1248
    • (1986) Tetrahedron Lett , vol.27 , pp. 1245-1248
    • Simonyan, S.O.1    Smit, W.A.2    Gybin, A.S.3    Schashkov, A.S.4    Mikaelian, G.S.5    Tarasov, V.A.6    Ibragimov, I.I.7    Caple, R.8    Froen, D.E.9
  • 41
    • 85082662233 scopus 로고
    • Cyclization of dicobalthexacarbonyl complexes of allyl propargyl ethers on the surface of chromatography adsorbents. A convenient method for the preparation of substituted 3-oxabicyclo [3.3.0]oct-5-en-7-one and 4- hydroxymethyl-2-cyclopenten-1-one derivatives from common precursors
    • Smit, W.A.; Simonyan, S.O.; Tarasov, V.A.; Mikaelian, G.S.; Gybin, A.S.; Ibragimov, I.I.; Caple, R.; Froen, D.; Kreager, A. Cyclization of dicobalthexacarbonyl complexes of allyl propargyl ethers on the surface of chromatography adsorbents. A convenient method for the preparation of substituted 3-oxabicyclo [3.3.0]oct-5-en-7-one and 4- hydroxymethyl-2-cyclopenten-1-one derivatives from common precursors. Synthesis 1989, 472-476.
    • (1989) Synthesis , pp. 472-476
    • Smit, W.A.1    Simonyan, S.O.2    Tarasov, V.A.3    Mikaelian, G.S.4    Gybin, A.S.5    Ibragimov, I.I.6    Caple, R.7    Froen, D.8    Kreager, A.9
  • 44
    • 0000252377 scopus 로고
    • Practical synthesis of unnatural (+)-physostigmine and carbamate analogues
    • Yu, Q.-S.; Brossi, A. Practical synthesis of unnatural (+)-physostigmine and carbamate analogues. Heterocycles 1988, 27, 745-750.
    • (1988) Heterocycles , vol.27 , pp. 745-750
    • Yu, Q.-S.1    Brossi, A.2
  • 46
    • 0036263802 scopus 로고    scopus 로고
    • A short synthesis of (±)-13- deoxyserratine
    • Cassayre, J.; Gagosz, F.; Zard, S.Z. A short synthesis of (±)-13- deoxyserratine. Angew. Chem. Int. Ed. 2002, 41, 1783-1785.
    • (2002) Angew. Chem. Int. Ed , vol.41 , pp. 1783-1785
    • Cassayre, J.1    Gagosz, F.2    Zard, S.Z.3
  • 47
    • 58849165652 scopus 로고    scopus 로고
    • Narjes, F. Discovery of pentacyclic compounds as potent inhibitors of hepatitis C virus NS5B RNA polymerase
    • Habermann, J.; Capitò, E.; Rico Ferreira, M.D.R.; Koch, U.; Narjes, F. Discovery of pentacyclic compounds as potent inhibitors of hepatitis C virus NS5B RNA polymerase. Bioorg. Med. Chem. Lett. 2009, 19, 633-638.
    • (2009) Bioorg. Med. Chem. Lett , vol.19 , pp. 633-638
    • Habermann, J.1    Capitò, E.2    Rico Ferreira, M.D.R.3    Koch, U.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.