메뉴 건너뛰기




Volumn 3, Issue 11, 2008, Pages 1839-1870

General approach to the total synthesis of macroline-related sarpagine and ajmaline alkaloids

Author keywords

Bisindoles; Enolate cross coupling; Macroline; Methoxytryptophans; Regiospecific hydroboration; Tollens reaction

Indexed keywords

2 EPIDIACETYLAJMALINE; AJMALINE; ALKALOID DERIVATIVE; ALSTONERINE; ANHYDROMACROSALHINE METHINE; ANTIPROTOZOAL AGENT; CHLOROQUINE; DIACETYLAJMALINE; DISPEGATRINE; EMETINE; GLAUCINE; INDOLE ALKALOID; KOUMINE; MACRALSTONINE O ACETATE; MACROCARPAMINE; N A METHYL 16 EPIPERICYCLIVINE; N A METHYL TETRACYCLIC KETONE; N A METHYLVELLOSIMINE; NORMACUSINE; NORSUAVEOLINE; PALLADIUM; RAUMACLINE; SARPAGINE; SPEGATRINE; SUAVEOLINE; TALCARPINE; TALPININE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VELLOSIMINE; VILLALSTONINE;

EID: 70449448857     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: None     Document Type: Review
Times cited : (21)

References (178)
  • 1
    • 77954198325 scopus 로고    scopus 로고
    • This paper is dedicated to Professor Wilfred R. Chan for his inspiration and dedication to natural products chemistry
    • This paper is dedicated to Professor Wilfred R. Chan for his inspiration and dedication to natural products chemistry.
  • 3
    • 0344503253 scopus 로고
    • Alkaloids derived from tryptophan
    • Mothes K, Schütte HR, Luckner M. (Eds.). VCH Publishers: Florida
    • Gröger D. (1985) Alkaloids derived from tryptophan. In Biochemistry of Alkaloids. Mothes K, Schütte HR, Luckner M. (Eds.). VCH Publishers: Florida, 272-313.
    • (1985) Biochemistry of Alkaloids , pp. 272-313
    • Gröger, D.1
  • 7
    • 0004190319 scopus 로고
    • 4 th Ed, J. and A. Churchill LTD: London
    • (b) Henry JA. (1949) The Plant Alkaloids, 4 th Ed, J. and A. Churchill LTD: London.
    • (1949) The Plant Alkaloids
    • Henry, J.A.1
  • 8
    • 0010344581 scopus 로고
    • Macralstonine, an alkaloid of the trunk bark of Alstonia macrophylla
    • Talapatra SK, Chaudhury NA. (1958) Macralstonine, an alkaloid of the trunk bark of Alstonia macrophylla. Science and Culture, 24, 243-245.
    • (1958) Science and Culture , vol.24 , pp. 243-245
    • Talapatra, S.K.1    Chaudhury, N.A.2
  • 9
    • 77954182187 scopus 로고
    • Studies on Philippine medicinal plants II. Further studies on the alkaloids of Alstonia macrophylla
    • Isidro N, Manalo GD. (1967) Studies on Philippine medicinal plants II. Further studies on the alkaloids of Alstonia macrophylla. Journal of the Philippine Pharmaceutical Association, 53(1-2), 9-19.
    • (1967) Journal of the Philippine Pharmaceutical Association , vol.53 , Issue.1-2 , pp. 9-19
    • Isidro, N.1    Manalo, G.D.2
  • 11
    • 0032968050 scopus 로고    scopus 로고
    • Cytoxic activity of indole alkaloids of three Alstonia species from Thailand
    • (a) Keawpradub N, Eno-Amooquaye E, Burke PJ, Houghton PJ. (1999) Cytoxic activity of indole alkaloids of three Alstonia species from Thailand. Planta Medica, 65, 311-315.
    • (1999) Planta Medica , vol.65 , pp. 311-315
    • Keawpradub, N.1    Eno-Amooquaye, E.2    Burke, P.J.3    Houghton, P.J.4
  • 12
    • 0032714668 scopus 로고    scopus 로고
    • Antiplasmodial activity of extracts and alkaloids of three Alstonia species from Thailand
    • (b) Keawpradub N, Kirby GC, Steele JC, Houghton PJ. (1999) Antiplasmodial activity of extracts and alkaloids of three Alstonia species from Thailand. Planta Medica, 65, 690-694.
    • (1999) Planta Medica , vol.65 , pp. 690-694
    • Keawpradub, N.1    Kirby, G.C.2    Steele, J.C.3    Houghton, P.J.4
  • 15
    • 0022438108 scopus 로고
    • Comparison of the effects of spegatrine and dispegatrine on α-adrenoceptors
    • (a) Feng Y, Gao H, Zeng G. (1986) Comparison of the effects of spegatrine and dispegatrine on α-adrenoceptors. Yaoxue Xuebao, 21, 1-6.
    • (1986) Yaoxue Xuebao , vol.21 , pp. 1-6
    • Feng, Y.1    Gao, H.2    Zeng, G.3
  • 16
    • 0022660112 scopus 로고
    • Quaternary alkaloids of Rauwolfia verticillata (Lour.) Baill var. Hainanensis tsiang
    • (b) Lin M, Yang B, Yu D. (1986) Quaternary alkaloids of Rauwolfia verticillata (Lour.) Baill var. Hainanensis tsiang. Yaoxue Xuebao, 21, 114-118.
    • (1986) Yaoxue Xuebao , vol.21 , pp. 114-118
    • Lin, M.1    Yang, B.2    Yu, D.3
  • 17
    • 77954201847 scopus 로고
    • Australian trees and high blood pressure
    • Elderfield RC. (1960) Australian trees and high blood pressure. American Scientist, 48, 193-208.
    • (1960) American Scientist , vol.48 , pp. 193-208
    • Elderfield, R.C.1
  • 23
    • 0017821908 scopus 로고
    • Biomimetic transformations among monomeric macroline-related indole alkaloids
    • Garnick RL, LeQuesne PW. (1978) Biomimetic transformations among monomeric macroline-related indole alkaloids. Journal of the American Chemical Society, 100, 4213-4219.
    • (1978) Journal of the American Chemical Society , vol.100 , pp. 4213-4219
    • Garnick, R.L.1    LeQuesne, P.W.2
  • 25
    • 77956691508 scopus 로고    scopus 로고
    • The Sarpagine Group of Indole Alkaloids
    • Cordell G. (Ed.). Academic Press
    • (a) Lounasmaa M, Hanhinen P, Westersund M. (1999) The Sarpagine Group of Indole Alkaloids. In The Alkaloids. Vol 52, Cordell G. (Ed.). Academic Press, 103-195.
    • (1999) The Alkaloids , vol.52 , pp. 103-195
    • Lounasmaa, M.1    Hanhinen, P.2    Westersund, M.3
  • 26
    • 0035238311 scopus 로고    scopus 로고
    • The Ajmaline Group of Indole Alkaloids
    • Cordell G. (Ed.). Academic Press
    • (b) Lounasmaa M, Hanhinen P. (2001) The Ajmaline Group of Indole Alkaloids. In The Alkaloids. Vol 55, Cordell G. (Ed.). Academic Press, 1-87.
    • (2001) The Alkaloids , vol.55 , pp. 1-87
    • Lounasmaa, M.1    Hanhinen, P.2
  • 27
    • 0000796316 scopus 로고
    • The Synthesis of Macroline Related Alkaloids
    • Basha FZ, Rahman A. (Eds.). Elsevier Science: Amsterdam
    • (a) Bi Y, Hamaker LK, Cook JM. (1993) The Synthesis of Macroline Related Alkaloids. In Bioactive Natural Products. Part A. Vol 13, Basha FZ, Rahman A. (Eds.). Elsevier Science: Amsterdam, 383-432.
    • (1993) Bioactive Natural Products. Part A , vol.13 , pp. 383-432
    • Bi, Y.1    Hamaker, L.K.2    Cook, J.M.3
  • 28
    • 0002452680 scopus 로고
    • The Synthesis of Macroline Related Sarpagine Alkaloids
    • Pelletier SW. (Ed.). Elsevier Science: New York
    • (b) Hamaker LK, Cook JM. (1995) The Synthesis of Macroline Related Sarpagine Alkaloids. In Alkaloids: Chemical and Biological Perspectives. Vol 9, Pelletier SW. (Ed.). Elsevier Science: New York, 23-84.
    • (1995) Alkaloids: Chemical and Biological Perspectives , vol.9 , pp. 23-84
    • Hamaker, L.K.1    Cook, J.M.2
  • 29
    • 0013848559 scopus 로고
    • Uniform numbering system for indole alkaloids
    • LeMen J, Taylor WI. (1965) Uniform numbering system for indole alkaloids. Experientia, 21, 508-510.
    • (1965) Experientia , vol.21 , pp. 508-510
    • LeMen, J.1    Taylor, W.I.2
  • 30
    • 0020571389 scopus 로고
    • The Sarpagine-Ajmaline Group of Indole Alkaloids
    • Herz W, Grisebach H, Kirby GW. (Eds.). Springer-Verlag: New York
    • Koskinen A, Lounasmaa M. (1983) The Sarpagine-Ajmaline Group of Indole Alkaloids. In Progress in the Chemistry of Organic Natural Products. Vol 43, Herz W, Grisebach H, Kirby GW. (Eds.). Springer-Verlag: New York, 267-346.
    • (1983) Progress in the Chemistry of Organic Natural Products , vol.43 , pp. 267-346
    • Koskinen, A.1    Lounasmaa, M.2
  • 31
    • 0043216517 scopus 로고
    • The Monoterpenoid Indole Alkaloids
    • Saxton JE. (Ed.). John Wiley and Sons: NewYork
    • (a) Creasey WA. (1983) The Monoterpenoid Indole Alkaloids. In Heterocyclic Compounds. Indole Series, Vol 25, Saxton JE. (Ed.). John Wiley and Sons: NewYork, 783-829.
    • (1983) Heterocyclic Compounds. Indole Series , vol.25 , pp. 783-829
    • Creasey, W.A.1
  • 32
    • 0030581467 scopus 로고    scopus 로고
    • What to do in patients with no structural heart disease and sudden arrhythmic death?
    • (b) Brugada J, Brugada P. (1996) What to do in patients with no structural heart disease and sudden arrhythmic death? The American Journal of Cardiology, 78, 69-75.
    • (1996) The American Journal of Cardiology , vol.78 , pp. 69-75
    • Brugada, J.1    Brugada, P.2
  • 33
    • 0001782987 scopus 로고
    • New development in the chemistry of natural substances
    • Woodward RB. (1956) New development in the chemistry of natural substances. Angewandte Chemie, 68, 13-20.
    • (1956) Angewandte Chemie , vol.68 , pp. 13-20
    • Woodward, R.B.1
  • 35
    • 0014232480 scopus 로고
    • Hypohalite-induced oxidative decarboxylation of α-amino acids
    • (b) van Tamelen EE, Haarstad VB, Orvis RL. (1968) Hypohalite-induced oxidative decarboxylation of α-amino acids. Tetrahedron, 24, 687-704.
    • (1968) Tetrahedron , vol.24 , pp. 687-704
    • Van Tamelen, E.E.1    Haarstad, V.B.2    Orvis, R.L.3
  • 36
    • 0019970279 scopus 로고
    • Biogenesis of the ajmaline type alkaloids
    • (a) Koskinen A, Lounasmaa M. (1982) Biogenesis of the ajmaline type alkaloids. Planta Medica, 45, 248-249.
    • (1982) Planta Medica , vol.45 , pp. 248-249
    • Koskinen, A.1    Lounasmaa, M.2
  • 37
    • 0021023503 scopus 로고
    • Biogenetic link between sarpagine and ajmaline type alkaloids
    • (b) Pfitzner A, Stöckigt J. (1983) Biogenetic link between sarpagine and ajmaline type alkaloids. Tetrahedron Letters, 24, 5197-5200.
    • (1983) Tetrahedron Letters , vol.24 , pp. 5197-5200
    • Pfitzner, A.1    Stöckigt, J.2
  • 38
    • 0000667057 scopus 로고    scopus 로고
    • The gene encoding polyneuridine aldehyde esterase of monoterpenoid indole alkaloid biosynthesis in plants is an ortholog of the alpha/beta hydrolase super family
    • DOI 10.1046/j.1432-1327.2000.01136.x
    • (c) Dogru E, Warzecha H, Seibel F, Haebel S, Lottspeich F, Stöckigt, J. (2000) The gene encoding polyneuridine aldehyde esterase of monoterpenoid indole alkaloid biosynthesis in plants is an ortholog of the alpha/betahydrolase super family. European Journal of Biochemistry, 267, 1397-1406. (Pubitemid 30143278)
    • (2000) European Journal of Biochemistry , vol.267 , Issue.5 , pp. 1397-1406
    • Dogru, E.1    Warzecha, H.2    Seibel, F.3    Haebel, S.4    Lottspeich, F.5    Stockigt, J.6
  • 39
    • 24644445180 scopus 로고    scopus 로고
    • Alkaloid biosynthesis in Rauvolfia- CDNA cloning of major enzymes of the ajmaline pathway
    • DOI 10.2174/138527205774370540
    • (d) Ruppert M, Ma X, Stöckigt J. (2005) Alkaloid biosynthesis in Rauvolfia -cDNA cloning of major enzymes of the ajmaline pathway. Current Organic Chemistry, 9, 1431-1444. (Pubitemid 41264294)
    • (2005) Current Organic Chemistry , vol.9 , Issue.15 , pp. 1431-1444
    • Ruppert, M.1    Ma, X.2    Stockigt, J.3
  • 40
    • 33746794215 scopus 로고    scopus 로고
    • Recent advances in the chemistry of macroline, sarpagine and ajmaline-related indole alkaloids
    • Lewis SE. (2006) Recent advances in the chemistry of macroline, sarpagine and ajmaline-related indole alkaloids. Tetrahedron, 62, 8655-8681.
    • (2006) Tetrahedron , vol.62 , pp. 8655-8681
    • Lewis, S.E.1
  • 42
    • 0042786709 scopus 로고
    • b-benzyl promoted retention of optical activity in the synthesis of an indolo substituted azabicyclo [3.3.1] nonane, a key template for the synthesis of macroline alkaloids
    • b-benzyl promoted retention of optical activity in the synthesis of an indolo substituted azabicyclo [3.3.1] nonane, a key template for the synthesis of macroline alkaloids. Heterocycles, 27, 2795-2803.
    • (1988) Heterocycles , vol.27 , pp. 2795-2803
    • Zhang, L.H.1    Cook, J.M.2
  • 43
    • 0013780435 scopus 로고
    • Synthesis of 12-methyl-1,2,3,4,6,7,12,12b-octahydro-2,6-methanoindolo[2, 3-a]quinolizine
    • (a) Yoneda N. (1965) Synthesis of 12-methyl-1,2,3,4,6,7,12,12b-octahydro- 2,6-methanoindolo[2,3-a]quinolizine. Chemical and Pharmacetical Bulletin, 13, 1231-1240.
    • (1965) Chemical and Pharmacetical Bulletin , vol.13 , pp. 1231-1240
    • Yoneda, N.1
  • 45
    • 4243241249 scopus 로고
    • The Pictet Spengler condensation: New directions for an old reaction
    • (a) Cox E, Cook JM. (1995) The Pictet Spengler condensation: New directions for an old reaction. Chemical Reviews, 95, 1797-1842.
    • (1995) Chemical Reviews , vol.95 , pp. 1797-1842
    • Cox, E.1    Cook, J.M.2
  • 46
    • 0000776419 scopus 로고    scopus 로고
    • Stereochemical control of the Pictet-Spengler reaction in the synthesis of natural products
    • Pearson W. (Ed.). JAI Press: Greenwich
    • (b) Czerwinski K, Cook JM. (1996) Stereochemical control of the Pictet-Spengler reaction in the synthesis of natural products. Advances in Heterocyclic Natural Product Synthesis. Vol 3, Pearson W. (Ed.). JAI Press: Greenwich, 217-277.
    • (1996) Advances in Heterocyclic Natural Product Synthesis. , vol.3 , pp. 217-277
    • Czerwinski, K.1    Cook, J.M.2
  • 48
    • 0000954063 scopus 로고
    • General approach to the synthesis of macroline-related alkaloids. Stereospecific total synthesis of (-)- Alstonerine
    • Zhang LH, Cook JM. (1990) General approach to the synthesis of macroline-related alkaloids. Stereospecific total synthesis of (-)- alstonerine. Journal of the American Chemical Society, 112, 4088-4090.
    • (1990) Journal of the American Chemical Society , vol.112 , pp. 4088-4090
    • Zhang, L.H.1    Cook, J.M.2
  • 49
    • 0027222086 scopus 로고
    • General approach for the synthesis of macroline/sarpagine alkaloids. The total synthesis of (+)-macroline
    • (a) Bi Y, Cook JM. (1993) General approach for the synthesis of macroline/sarpagine alkaloids. The total synthesis of (+)-macroline. Tetrahedron Letters, 34, 4501-4504.
    • (1993) Tetrahedron Letters , vol.34 , pp. 4501-4504
    • Bi, Y.1    Cook, J.M.2
  • 50
    • 0028151059 scopus 로고
    • Enantiospecific synthesis of (-)-alstonerine and (+)-macroline as well as a partial synthesis of (+)-villalstonine
    • DOI 10.1021/ja00099a021
    • (b) Bi Y, Zhang L-H, Hamaker LK, Cook JM. (1994) Enantiospecific synthesis of (-)-alstonerine and (+)-macroline as well as a partial synthesis of (+)-villalstonine. Journal of the American Chemical Society, 116, 9027-9041. (Pubitemid 24336952)
    • (1994) Journal of the American Chemical Society , vol.116 , Issue.20 , pp. 9027-9041
    • Bi, Y.1    Zhang, L.-H.2    Hamaker, L.K.3    Cook, J.M.4
  • 51
    • 0030586109 scopus 로고    scopus 로고
    • General approach for the synthesis of macroline/sarpagine related indole alkaloids via the asymmetric Pictet-Spengler reaction: The enantiospecific synthesis of (-)-anhydromacrosalhine-methine
    • DOI 10.1016/0040-4039(96)01009-X
    • (a) Gan T, Cook JM. (1996) General approach for the synthesis of macroline/sarpagine related indole alkaloids via the asymmetric Pictet-Spengler reaction: The enantiospecific synthesis of (-)-anhydromacrosalhine-methine. Tetrahedron Letters, 37, 5033-5036. (Pubitemid 26315254)
    • (1996) Tetrahedron Letters , vol.37 , Issue.29 , pp. 5033-5036
    • Gan, T.1    Cook, J.M.2
  • 52
    • 0030586099 scopus 로고    scopus 로고
    • Partial synthesis of the antiamoebic bisindole alkaloid (-)- Macrocarpamine
    • DOI 10.1016/0040-4039(96)01010-6
    • (b) Gan T, Cook JM. (1996) Partial synthesis of the antiamoebic bisindole alkaloid (-)-macrocarpamine. Tetrahedron Letters, 37, 5037-5038. (Pubitemid 26315255)
    • (1996) Tetrahedron Letters , vol.37 , Issue.29 , pp. 5037-5038
    • Gan, T.1    Cook, J.M.2
  • 53
    • 0032489338 scopus 로고    scopus 로고
    • Enantiospecific total synthesis of (-)-anhydromacrosalhine-methine and partial synthesis of the antiamoebic bisindole alkaloid (-)-macrocarpamine
    • DOI 10.1021/jo971570t
    • (c) Gan T, Cook JM. (1998) Enantiospecific total synthesis of (-)-anhydromacrosalhine-methine and partial synthesis of the antiamoebic bisindole alkaloid (-)-macrocarpamine. The Journal of Organic Chemistry, 63, 1478-1483. (Pubitemid 28136909)
    • (1998) Journal of Organic Chemistry , vol.63 , Issue.5 , pp. 1478-1483
    • Gan, T.1    Cook, J.M.2
  • 54
    • 0028364925 scopus 로고
    • A partial synthesis of the Alstonia bisindole alkaloid villalstonine
    • DOI 10.1016/S0040-4039(00)76690-1
    • Bi Y, Cook JM, LeQuesne PW. (1994) Partial synthesis of the Alstonia bisindole alkaloid villalstonine. Tetrahedron Letters, 35, 3877-3878. (Pubitemid 24199596)
    • (1994) Tetrahedron Letters , vol.35 , Issue.23 , pp. 3877-3878
    • Bi, Y.1    Cook, J.M.2    LeQuesne, P.W.3
  • 57
    • 37049083704 scopus 로고
    • Use of the kinetically controlled Pictet-Spengler reaction in the asymmetric synthesis of indole alkaloids: Formal syntheses of (-)-ajmaline, (-)-koumine, (-)-taberpsychine, (-)-koumidine and (-)-suaveoline
    • For alternate syntheses of raumacline and suaveoline refer : (1)
    • (c) For alternate syntheses of raumacline and suaveoline refer : (1) Bailey PD, McLay NR. (1993) Use of the kinetically controlled Pictet-Spengler reaction in the asymmetric synthesis of indole alkaloids: Formal syntheses of (-)-ajmaline, (-)-koumine, (-)-taberpsychine, (-)-koumidine and (-)-suaveoline. Journal of the Chemical Society, Perkin Transaction 1: Organic and Bio-organic chemistry, 4, 441-449.
    • (1993) Journal of the Chemical Society, Perkin Transaction 1: Organic and Bio-organic Chemistry , vol.4 , pp. 441-449
    • Bailey, P.D.1    McLay, N.R.2
  • 59
    • 4143076856 scopus 로고    scopus 로고
    • Total synthesis of suaveoline and norsuaveoline via intramolecular oxazole-olefin Diels-Alder reaction
    • Ohba M, Natsutani I, Sakuma T. (2004) Total synthesis of suaveoline and norsuaveoline via intramolecular oxazole-olefin Diels-Alder reaction. Tetrahedron Letters, 45, 6471-6474.
    • (2004) Tetrahedron Letters , vol.45 , pp. 6471-6474
    • Ohba, M.1    Natsutani, I.2    Sakuma, T.3
  • 60
    • 0031835026 scopus 로고    scopus 로고
    • A straightforward preparation of chiral 5-(aminomethyl)oxazole derivatives from α-aminoesters and α-lithiated isocyanides
    • Ohba M, Kubo H, Seto S, Fujii T, Ishibashi H. (1998) A straightforward preparation of chiral 5-(aminomethyl)oxazole derivatives from α-aminoesters and α-lithiated isocyanides. Chemical and Pharmacetical Bulletin, 46, 860-862.
    • (1998) Chemical and Pharmacetical Bulletin , vol.46 , pp. 860-862
    • Ohba, M.1    Kubo, H.2    Seto, S.3    Fujii, T.4    Ishibashi, H.5
  • 61
    • 0025148857 scopus 로고
    • Studies on Gelsemium alkaloids. Total synthesis of (+)-koumine, (+)- Taberpsychine, and (+)-koumidine
    • Magnus P, Mugrage B, Deluca MR, Cain GA. (1990) Studies on Gelsemium alkaloids. Total synthesis of (+)-koumine, (+)- taberpsychine, and (+)-koumidine. Journal of the American Chemical Society, 112, 5220-5230.
    • (1990) Journal of the American Chemical Society , vol.112 , pp. 5220-5230
    • Magnus, P.1    Mugrage, B.2    Deluca, M.R.3    Cain, G.A.4
  • 62
    • 0025813443 scopus 로고
    • Asymmetric synthesis of indole alkaloids from (L)-tryptophan: Formal syntheses of (-)- Koumine, (-)-taberpsychine and (-)-koumidine
    • Bailey PD, McLay NR. (1991) Asymmetric synthesis of indole alkaloids from (L)-tryptophan: Formal syntheses of (-)- koumine, (-)-taberpsychine and (-)-koumidine. Tetrahedron Letters, 32, 3895-3898.
    • (1991) Tetrahedron Letters , vol.32 , pp. 3895-3898
    • Bailey, P.D.1    McLay, N.R.2
  • 64
    • 0034685733 scopus 로고    scopus 로고
    • Enantiospecific total synthesis of the sarpagine related indole alkaloids talpinine and talcarpine as well as the improved total synthesis of alstonerine and anhydromacrosalhinemethine via the asymmetric Pictet-Spengler reaction
    • (b) Yu P, Wang T, Li J, Cook JM. (2000) Enantiospecific total synthesis of the sarpagine related indole alkaloids talpinine and talcarpine as well as the improved total synthesis of alstonerine and anhydromacrosalhinemethine via the asymmetric Pictet-Spengler reaction. The Journal of Organic Chemistry, 65, 3173-3191.
    • (2000) The Journal of Organic Chemistry , vol.65 , pp. 3173-3191
    • Yu, P.1    Wang, T.2    Li, J.3    Cook, J.M.4
  • 65
    • 77954182833 scopus 로고
    • Synthetic approaches to alkaloids of the sarpagine and ajmaline groups. I. Preparation of some tetracyclic intermediates
    • (a) Hobson JD, Raines J, Whiteoak RJ. (1963) Synthetic approaches to alkaloids of the sarpagine and ajmaline groups. I. Preparation of some tetracyclic intermediates. Journal of the Chemical Society, 349-503.
    • (1963) Journal of the Chemical Society , pp. 349-503
    • Hobson, J.D.1    Raines, J.2    Whiteoak, R.J.3
  • 66
    • 0021237769 scopus 로고
    • Asymmetric synthesis and absolute configuration of (-)-trypargine
    • (b) Shimizu M, Ishikawa M, Komoda Y, Nakajima T, Yamaguchi K, Sakai S. (1984) Asymmetric synthesis and absolute configuration of (-)-trypargine. Chemical and Pharmaceutical Bulletin, 32, 1313-1325. (Pubitemid 14101048)
    • (1984) Chemical and Pharmaceutical Bulletin , vol.32 , Issue.4 , pp. 1313-1325
    • Shimizu, M.1    Ishikawa, M.2    Komoda, Y.3
  • 67
    • 0020537546 scopus 로고
    • Selenium dioxide oxidations in the indole area. Synthesis of β-carboline alkaloids
    • (c) Cain M, Campos O, Guzman F, Cook JM. (1983) Selenium dioxide oxidations in the indole area. Synthesis of β-carboline alkaloids. Journal of the American Chemical Society, 105, 907-913. (Pubitemid 13135812)
    • (1983) Journal of the American Chemical Society , vol.105 , Issue.4 , pp. 907-913
    • Cain, M.1    Campos, O.2    Guzman, F.3    Cook, J.M.4
  • 72
    • 0034731150 scopus 로고    scopus 로고
    • A stereospecific synthesis of (±)-5,8-disubstituted indolizidines and (±)-1,4-disubstituted quinolizidines found in poison frog skins
    • DOI 10.1021/jo000666b
    • (a) Michel P, Rassat A, Daly JW, Spande TF. (2000) A stereospecific synthesis of (±)-5, 8-disubstituted indolizidines and (±)-1, 4-disubstituted quinolizidines found in poison frog skins. The Journal of Organic Chemistry, 65, 8908-8918. (Pubitemid 32015145)
    • (2000) Journal of Organic Chemistry , vol.65 , Issue.26 , pp. 8908-8918
    • Michel, P.1    Rassat, A.2    Daly, J.W.3    Spande, T.F.4
  • 73
    • 0034091818 scopus 로고    scopus 로고
    • (endo, endo)-9-Benzyl-9-azabicyclo [3.3.1] nonane-2, 6-diol: An intermediate for the preparation of indole alkaloids of the macroline/sarpagine series
    • (b) Gennet D, Michel P, Rassat A. (2000) (endo, endo)-9-Benzyl-9- azabicyclo [3.3.1] nonane-2, 6-diol: An intermediate for the preparation of indole alkaloids of the macroline/sarpagine series. Synthesis, 3, 447-451.
    • (2000) Synthesis , vol.3 , pp. 447-451
    • Gennet, D.1    Michel, P.2    Rassat, A.3
  • 75
    • 0242576783 scopus 로고    scopus 로고
    • Synthesis of bridged azabicyclic structures via ring-closing olefin metathesis
    • (d) Neipp CE, Martin SF. (2003) Synthesis of bridged azabicyclic structures via ring-closing olefin metathesis. The Journal of Organic Chemistry, 68, 8867-8878.
    • (2003) The Journal of Organic Chemistry , vol.68 , pp. 8867-8878
    • Neipp, C.E.1    Martin, S.F.2
  • 79
    • 0017165780 scopus 로고
    • The biogenetic-type total synthesis of ajmaline
    • (b) van Tamelen EE, Oliver LK. (1976) The biogenetic-type total synthesis of ajmaline. Bioorganic Chemistry, 5, 309-326.
    • (1976) Bioorganic Chemistry , vol.5 , pp. 309-326
    • Van Tamelen, E.E.1    Oliver, L.K.2
  • 81
    • 37049133259 scopus 로고
    • Cleavage of tertiary bases with phenyl chloroformate. Reconversion of 21-deoxyajmaline into ajmaline
    • Hobson JD, McCluskey JG. (1967) Cleavage of tertiary bases with phenyl chloroformate. Reconversion of 21-deoxyajmaline into ajmaline. Journal of the Chemical Society [Section]C: Organic, 20, 2015-2017.
    • (1967) Journal of the Chemical Society [Section]C: Organic , vol.20 , pp. 2015-2017
    • Hobson, J.D.1    McCluskey, J.G.2
  • 82
    • 0000656873 scopus 로고    scopus 로고
    • General approach to the synthesis of sarpagine and ajmaline alkaloids. Enantiospecific total synthesis of (+)-ajmaline and alkaloid G via the asymmetric Pictet- Spengler reaction
    • (a) Li J, Cook JM. (1998) General approach to the synthesis of sarpagine and ajmaline alkaloids. Enantiospecific total synthesis of (+)-ajmaline and alkaloid G via the asymmetric Pictet- Spengler reaction. The Journal of Organic Chemistry, 63, 4166-4167.
    • (1998) The Journal of Organic Chemistry , vol.63 , pp. 4166-4167
    • Li, J.1    Cook, J.M.2
  • 83
    • 0033523248 scopus 로고    scopus 로고
    • General approach for the synthesis of ajmaline/sarpagine indole alkaloids: Enantiospecific total synthesis of (+) ajmaline, alkaloid G, and norvsuaveoline via the asymmetric Pictet-Spengler reaction
    • (b) Li J, Wang T, Yu P, Peterson A, Soerens D, Weber D, Grubisha D, Bennett D, Cook JM. (1999) General approach for the synthesis of ajmaline/sarpagine indole alkaloids: Enantiospecific total synthesis of (+) ajmaline, alkaloid G, and norvsuaveoline via the asymmetric Pictet-Spengler reaction. Journal of the American Chemical Society, 121, 6998-7010.
    • (1999) Journal of the American Chemical Society , vol.121 , pp. 6998-7010
    • Li, J.1    Wang, T.2    Yu, P.3    Peterson, A.4    Soerens, D.5    Weber, D.6    Grubisha, D.7    Bennett, D.8    Cook, J.M.9
  • 84
    • 0001208130 scopus 로고
    • Direct insertion of alkali (alkaline earth) metals into allylic carbon-halogen bonds avoiding stereorandomization
    • (a) Yanagisawa A, Habaue S, Yamamoto H. (1991) Direct insertion of alkali (alkaline earth) metals into allylic carbon-halogen bonds avoiding stereorandomization. Journal of the American Chemical Society, 113, 5893-5895.
    • (1991) Journal of the American Chemical Society , vol.113 , pp. 5893-5895
    • Yanagisawa, A.1    Habaue, S.2    Yamamoto, H.3
  • 86
    • 85077990318 scopus 로고
    • Grignard reagents from chemically activated magnesium
    • For a review on the Grignard reactions see
    • (c) For a review on the Grignard reactions see: Lai Y-H. (1981) Grignard reagents from chemically activated magnesium. Synthesis, 8, 585-604.
    • (1981) Synthesis , vol.8 , pp. 585-604
    • Lai, Y.-H.1
  • 87
    • 84987123520 scopus 로고
    • The Barbier reaction- A one-step alternative for syntheses via organomagnesium compounds
    • For a review on the Barbier reaction see
    • For a review on the Barbier reaction see: Blomberg C, Hartog FA. (1977) The Barbier reaction- A one-step alternative for syntheses via organomagnesium compounds. Synthesis, 1, 18-30.
    • (1977) Synthesis , vol.1 , pp. 18-30
    • Blomberg, C.1    Hartog, F.A.2
  • 88
    • 0035825752 scopus 로고    scopus 로고
    • Stereocontrolled Total Synthesis of Alkaloid G via the Oxy-anion Cope Rearrangement and Improved Total Synthesis of (+)-Ajmaline
    • DOI 10.1021/ol000331g
    • (a) Wang T, Xu Q, Yu P, Liu X, Cook JM. (2001) Stereocontrolled total synthesis of alkaloid G via the oxy-anion Cope rearrangement and improved total synthesis of (+)-ajmaline. Organic Letters, 3, 345-348. (Pubitemid 33692991)
    • (2001) Organic Letters , vol.3 , Issue.3 , pp. 345-348
    • Wang, T.1    Xu, Q.2    Yu, P.3    Liu, X.4    Cook, J.M.5
  • 91
    • 0000747645 scopus 로고
    • Dichlorodicyanoquinone oxidations in the indole area. Synthesis of crenatine
    • Cain M, Mantei R, Cook JM. (1982) Dichlorodicyanoquinone oxidations in the indole area. Synthesis of crenatine. The Journal of Organic Chemistry, 47, 4933-4936.
    • (1982) The Journal of Organic Chemistry , vol.47 , pp. 4933-4936
    • Cain, M.1    Mantei, R.2    Cook, J.M.3
  • 92
    • 0000450576 scopus 로고
    • Selective oxidation of the side chain at C-3 of indoles
    • (a) Oikawa Y, Yonemitsu O. (1977) Selective oxidation of the side chain at C-3 of indoles. The Journal of Organic Chemistry, 42, 1213-1216.
    • (1977) The Journal of Organic Chemistry , vol.42 , pp. 1213-1216
    • Oikawa, Y.1    Yonemitsu, O.2
  • 93
    • 0000980557 scopus 로고
    • Synthesis of pimprinine and related oxazolylindole alkaloids from N-acyl derivatives of tryptamine and tryptophan methyl ester by DDQ oxidation
    • (b) Oikawa Y, Yoshioka T, Kunihiko M, Yonemitsu O. (1979) Synthesis of pimprinine and related oxazolylindole alkaloids from N-acyl derivatives of tryptamine and tryptophan methyl ester by DDQ oxidation. Heterocycles, 12, 1457-1462.
    • (1979) Heterocycles , vol.12 , pp. 1457-1462
    • Oikawa, Y.1    Yoshioka, T.2    Kunihiko, M.3    Yonemitsu, O.4
  • 94
    • 0026020179 scopus 로고
    • An efficient synthetic pathway to the macroline-type indole alkaloids, talcarpine and alstonerine from ajmaline
    • Takayama H, Phisalaphong C, Kitajima M, Aimi N, Sakai S. (1991) An efficient synthetic pathway to the macroline-type indole alkaloids, talcarpine and alstonerine from ajmaline. Tetrahedron, 47, 1383-1392.
    • (1991) Tetrahedron , vol.47 , pp. 1383-1392
    • Takayama, H.1    Phisalaphong, C.2    Kitajima, M.3    Aimi, N.4    Sakai, S.5
  • 95
    • 33845559199 scopus 로고
    • N-Phenylselenophthalimide (N-PSP) and N-phenylselenosuccinimide (N-PSS). Two versatile carriers of the phenylseleno group. Oxyselenation of olefins and a selenium-based macrolide synthesis
    • Nicolaou KC, Claremon DA, Barnette WE, Seitz SP. (1979) N-Phenylselenophthalimide (N-PSP) and N-phenylselenosuccinimide (N-PSS). Two versatile carriers of the phenylseleno group. Oxyselenation of olefins and a selenium-based macrolide synthesis. Journal of the American Chemical Society, 101, 3704-3706.
    • (1979) Journal of the American Chemical Society , vol.101 , pp. 3704-3706
    • Nicolaou, K.C.1    Claremon, D.A.2    Barnette, W.E.3    Seitz, S.P.4
  • 96
    • 0015516842 scopus 로고
    • Indolalkaloids of Pleiocarpa talbotii Wernham. 145. Alkaloids
    • Naranjo J, Pinar M, Hesse M, Schmid H. (1972) Indolalkaloids of Pleiocarpa talbotii Wernham. 145. Alkaloids. Helvetica Chimica Acta, 55, 752-771.
    • (1972) Helvetica Chimica Acta , vol.55 , pp. 752-771
    • Naranjo, J.1    Pinar, M.2    Hesse, M.3    Schmid, H.4
  • 97
    • 0032509488 scopus 로고    scopus 로고
    • Enantiospecific total synthesis of the sarpagine related indole alkaloids talpinine and talcarpine: The oxyanion-cope approach
    • DOI 10.1021/jo981815h
    • Yu P, Cook JM. (1998) Enantiospecific total synthesis of the sarpagine related indole alkaloids talpinine and talcarpine: The oxyanion Cope approach. The Journal of Organic Chemistry, 63, 9160-9161. (Pubitemid 29008972)
    • (1998) Journal of Organic Chemistry , vol.63 , Issue.25 , pp. 9160-9161
    • Yu, P.1    Cook, J.M.2
  • 98
    • 0030730569 scopus 로고    scopus 로고
    • Diastereospecific synthesis of ketooxindoles. Potential intermediates for the synthesis of alstonisine as well as for voachalotine related oxindole alkaloids
    • Yu P, Cook JM. (1997) Diastereospecific synthesis of ketooxindoles. Potential intermediates for the synthesis of alstonisine as well as for voachalotine related oxindole alkaloids. Tetrahedron Letters, 38, 8799-8802.
    • (1997) Tetrahedron Letters , vol.38 , pp. 8799-8802
    • Yu, P.1    Cook, J.M.2
  • 99
    • 37049069964 scopus 로고
    • Stereoselective transformation of ajmaline into three minor Gelsemium alkaloids, koumidine, (19Z)-anhydrovobasinediol [(19Z)-taberpsychine] and N-demethoxyrankinidine and their absolute configuration
    • Kitajima M, Takayama H, Sakai S. (1991) Stereoselective transformation of ajmaline into three minor Gelsemium alkaloids, koumidine, (19Z)- anhydrovobasinediol [(19Z)-taberpsychine] and N-demethoxyrankinidine and their absolute configuration. Journal of Chemical Society, Perkin Transactions, 1, 1773-1779.
    • (1991) Journal of Chemical Society, Perkin Transactions , vol.1 , pp. 1773-1779
    • Kitajima, M.1    Takayama, H.2    Sakai, S.3
  • 100
    • 0033564999 scopus 로고    scopus 로고
    • An Enantioselective total synthesis of (+)-geissoschizine
    • Martin SF, Chen KX, Eary CT. (1999) An Enantioselective total synthesis of (+)-geissoschizine. Organic Letters, 1, 79-82.
    • (1999) Organic Letters , vol.1 , pp. 79-82
    • Martin, S.F.1    Chen, K.X.2    Eary, C.T.3
  • 101
    • 0027231508 scopus 로고
    • General strategy for the stereocontrolled synthesis of Strychnos alkaloids: A concise synthesis of (±)-dehydrotubifoline
    • (a) Rawal VH, Michoud C, Monestel R. (1993) General strategy for the stereocontrolled synthesis of Strychnos alkaloids: A concise synthesis of (±)-dehydrotubifoline. Journal of the American Chemical Society, 115, 3030-3031. (Pubitemid 23149253)
    • (1993) Journal of the American Chemical Society , vol.115 , Issue.7 , pp. 3030-3031
    • Rawal, V.H.1    Michoud, C.2    Monestel, R.F.3
  • 102
    • 0029557965 scopus 로고
    • Studies on the synthesis of Strychnos indole alkaloids. Synthesis of (±)-dihydrotubifoline
    • DOI 10.1021/ja00149a029
    • (b) Bonjoch J, Sole D, Bosch J. (1995) Studies on the synthesis of Strychnos indole alkaloids. Synthesis of (±)-dehydrotubifoline. Journal of the American Chemical Society, 117, 11017-11018. (Pubitemid 26056284)
    • (1995) Journal of the American Chemical Society , vol.117 , Issue.44 , pp. 11017-11018
    • Bonjoch, J.1    Sole, D.2    Bosch, J.3
  • 103
    • 0030840651 scopus 로고    scopus 로고
    • A general synthetic entry to Strychnos alkaloids of the curan type via a common 3a-(2-nitrophenyl)hexahydroindol-4-one intermediate. Total syntheses of (□)- And (-)-tubifolidine, (□)-akuammicine, (□)-19,20- dihydroakuammicine, (□)-norfluorocurarine, (□)-echitamidine, and (□)-20-epilochneridine
    • (c) Bonjoch J, Sole D, Garcia-Rubio S, Bosch J. (1997) A general synthetic entry to Strychnos alkaloids of the curan type via a common 3a-(2-nitrophenyl)hexahydroindol-4-one intermediate. Total syntheses of (□)- and (-)-tubifolidine, (□)-akuammicine, (□)-19,20-dihydroakuammicine, (□)-norfluorocurarine, (□)-echitamidine, and (□)-20-epilochneridine. Journal of the American Chemical Society, 119, 7230-7240.
    • (1997) Journal of the American Chemical Society , vol.119 , pp. 7230-7240
    • Bonjoch, J.1    Sole, D.2    Garcia-Rubio, S.3    Bosch, J.4
  • 104
    • 0034643989 scopus 로고    scopus 로고
    • General approach for the synthesis of sarpagine/ajmaline indole alkaloids. Stereospecific total synthesis of the sarpagine alkaloid (+)-vellosimine
    • (a) Wang T, Cook JM. (2000) General approach for the synthesis of sarpagine/ajmaline indole alkaloids. Stereospecific total synthesis of the sarpagine alkaloid (+)-vellosimine. Organic Letters, 2, 2057-2059.
    • (2000) Organic Letters , vol.2 , pp. 2057-2059
    • Wang, T.1    Cook, J.M.2
  • 105
    • 0037433930 scopus 로고    scopus 로고
    • 3and (-)-panarine via the asymmetric Pictet-Spengler reaction
    • 3 and (-)-panarine via the asymmetric Pictet-Spengler reaction. Tetrahedron Letters, 44, 543-547.
    • (2003) Tetrahedron Letters , vol.44 , pp. 543-547
    • Yu, J.1    Wearing, X.2    Cook, J.M.3
  • 108
    • 0029818921 scopus 로고    scopus 로고
    • Syntheses of Strychnos and Aspidospermatan-type alkaloids. 8. Selective total syntheses of mossambine and 14-epi-mossambine by a radical cyclization reaction
    • Kuehne ME, Wang T, Seraphin D. (1996) Syntheses of Strychnos and Aspidospermatan-type alkaloids. 8. Selective total syntheses of mossambine and 14-epi-mossambine by a radical cyclization reaction. The Journal of Organic Chemistry, 61, 7873-7881.
    • (1996) The Journal of Organic Chemistry , vol.61 , pp. 7873-7881
    • Kuehne, M.E.1    Wang, T.2    Seraphin, D.3
  • 109
  • 110
    • 0028123008 scopus 로고
    • A biomimetic synthesis of a new skeletal Gelsemium alkaloid, 11-methoxy-19(R)-hydroxygelselegine
    • (b) Takayama H, Kitajima M, Sakai S. (1994) A biomimetic synthesis of a new skeletal Gelsemium alkaloid, 11-methoxy-19(R)-hydroxygelselegine. Tetrahedron, 50, 11813-11820.
    • (1994) Tetrahedron , vol.50 , pp. 11813-11820
    • Takayama, H.1    Kitajima, M.2    Sakai, S.3
  • 111
    • 0032192164 scopus 로고    scopus 로고
    • A novel route to the geissoschizine skeleton: The influence of ligands on the diastereoselectivity of the Heck cyclization
    • Birman VB, Rawal VH. (1998) A novel route to the geissoschizine skeleton: The influence of ligands on the diastereoselectivity of the Heck cyclization. Tetrahedron Letters, 39, 7219-7222.
    • (1998) Tetrahedron Letters , vol.39 , pp. 7219-7222
    • Birman, V.B.1    Rawal, V.H.2
  • 112
    • 0030861285 scopus 로고    scopus 로고
    • Palladium-catalyzed intramolecular α-arylation of aliphatic ketones
    • Muratake H, Natsume M. (1997) Palladium-catalyzed intramolecular α-arylation of aliphatic ketones. Tetrahedron Letters, 38, 7581-7582.
    • (1997) Tetrahedron Letters , vol.38 , pp. 7581-7582
    • Muratake, H.1    Natsume, M.2
  • 113
    • 0001703098 scopus 로고
    • A new five-membered ring annulation method based on palladium(0)- catalyzed intramolecular coupling of vinyl iodide and enolate anion functions
    • (a) Piers E, Marais PC (1990) A new five-membered ring annulation method based on palladium(0)-catalyzed intramolecular coupling of vinyl iodide and enolate anion functions. The Journal of Organic Chemistry, 55, 3454-3455.
    • (1990) The Journal of Organic Chemistry , vol.55 , pp. 3454-3455
    • Piers, E.1    Marais, P.C.2
  • 114
    • 0027396756 scopus 로고
    • Total synthesis of the tetraquinane diterpenoid (±)-crinipellin B
    • (b) Piers, E, Renaud, J. (1993) Total synthesis of the tetraquinane diterpenoid (±)-crinipellin B. The Journal of Organic Chemistry, 58, 11-13.
    • (1993) The Journal of Organic Chemistry , vol.58 , pp. 11-13
    • Piers, E.1    Renaud, J.2
  • 115
    • 0034641496 scopus 로고    scopus 로고
    • Enantiospecific total synthesis of the enantiomer of the indole alkaloid affinisine
    • Liu X, Wang T, Xu Q, Ma C, Cook JM. (2000) Enantiospecific total synthesis of the enantiomer of the indole alkaloid affinisine. Tetrahedron Letters, 41, 6299-6303.
    • (2000) Tetrahedron Letters , vol.41 , pp. 6299-6303
    • Liu, X.1    Wang, T.2    Xu, Q.3    Ma, C.4    Cook, J.M.5
  • 116
    • 0026763993 scopus 로고
    • Mild oxidation of aldehydes to the corresponding carboxylic acids and esters: Alkaline iodine oxidation revisited
    • Yamada S, Morizono D, Yamamoto K. (1992) Mild oxidation of aldehydes to the corresponding carboxylic acids and esters: Alkaline iodine oxidation revisited. Tetrahedron Letters, 33, 4329-4332.
    • (1992) Tetrahedron Letters , vol.33 , pp. 4329-4332
    • Yamada, S.1    Morizono, D.2    Yamamoto, K.3
  • 118
    • 0037037948 scopus 로고    scopus 로고
    • Enantiospecific total synthesis of the enantiomer of the indole alkaloid intermediate macroline
    • DOI 10.1016/S0040-4039(02)01729-X, PII S004040390201729X
    • (b) Liu X, Zhang C, Liao X, Cook JM. (2002) Enantiospecific total synthesis of the enantiomer of the indole alkaloid intermediate macroline. Tetrahedron Letters, 43, 7373-7377. (Pubitemid 35287115)
    • (2002) Tetrahedron Letters , vol.43 , Issue.41 , pp. 7373-7377
    • Liu, X.1    Zhang, C.2    Liao, X.3    Cook, J.M.4
  • 119
    • 0001941032 scopus 로고
    • Hydration of olefins, dienes, and acetylenes via hydroboration
    • Zweifel G, Brown HC. (1963) Hydration of olefins, dienes, and acetylenes via hydroboration. Organic Reactions, 13, 1-54.
    • (1963) Organic Reactions , vol.13 , pp. 1-54
    • Zweifel, G.1    Brown, H.C.2
  • 120
    • 0035856923 scopus 로고    scopus 로고
    • General approach for the synthesis of sarpagine/macroline indole alkaloids. Enantiospecific total synthesis of the indole alkaloid trinervine
    • Liu X, Cook JM. (2002) General approach for the synthesis of sarpagine/macroline indole alkaloids. Enantiospecific total synthesis of the indole alkaloid trinervine. Organic Letters, 3, 4023-4026.
    • (2002) Organic Letters , vol.3 , pp. 4023-4026
    • Liu, X.1    Cook, J.M.2
  • 122
    • 0019129934 scopus 로고
    • Binding of 5-fluoro-L-tryptophan to human serum albumin
    • DOI 10.1021/ja00532a052
    • Gerig JT, Klinkenborg JC. (1980) Binding of 5-fluoro-L-tryptophan to human serum albumin. Journal of the American Chemical Society, 102, 4267-4268. (Pubitemid 11242203)
    • (1980) Journal of the American Chemical Society , vol.102 , Issue.12 , pp. 4267-4268
    • Gerig, J.T.1    Klinkenborg, J.C.2
  • 124
    • 77954197070 scopus 로고
    • Cyclic tautomers of tryptophans and tryptamines II. Synthesis of 5-nitro-, 5-methoxy-, and 6-methoxy-tryptophan derivatives. Heterocycles, 12, 1027- 1030. (c) Irie K, Ishida A, Nakamura T, Oh-Ishi T. (1984) Syntheses of substituted L- and D-tryptophans
    • (b) Hino T, Taniguchi M, Gonsho A, Nakagawa M. (1979) Cyclic tautomers of tryptophans and tryptamines II. Synthesis of 5-nitro-, 5-methoxy-, and 6-methoxy-tryptophan derivatives. Heterocycles, 12, 1027- 1030. (c) Irie K, Ishida A, Nakamura T, Oh-Ishi T. (1984) Syntheses of substituted L- and D-tryptophans. Chemical and Pharmaceutical Bulletin, 32, 2126-2139.
    • (1979) Chemical and Pharmaceutical Bulletin , vol.32 , pp. 2126-2139
    • Hino, T.1    Taniguchi, M.2    Gonsho, A.3    Nakagawa, M.4
  • 125
    • 0031436451 scopus 로고    scopus 로고
    • Enantiospecific Synthesis of Optically Active 6-Methoxytryptophan Derivatives and Total Synthesis of Tryprostatin a
    • (a) Gan T, Liu R, Yu P, Zhao S, Cook JM. (1997) Enantiospecific synthesis of optically active 6-methoxytryptophan derivatives and total synthesis of tryprostatin A. The Journal of Organic Chemistry, 62, 9298-9304. (Pubitemid 128495950)
    • (1997) Journal of Organic Chemistry , vol.62 , Issue.26 , pp. 9298-9304
    • Gan, T.1    Liu, R.2    Yu, P.3    Zhao, S.4    Cook, J.M.5
  • 126
    • 0032563838 scopus 로고    scopus 로고
    • Total synthesis of tryprostatin a and B as well as their enantiomers
    • DOI 10.1016/S0040-4039(98)01466-X, PII S004040399801466X
    • (b) Zhao S, Gan T, Yu P, Cook JM. (1998) Total synthesis of tryprostatin A and B as well as their enantiomers. Tetrahedron Letters, 39, 7009-7012. (Pubitemid 28414769)
    • (1998) Tetrahedron Letters , vol.39 , Issue.39 , pp. 7009-7012
    • Zhao, S.1    Gan, T.2    Yu, P.3    Cook, J.M.4
  • 127
    • 0029133614 scopus 로고
    • An enantiospecific synthesis of L(-) and D(+)-6-Chloro-5- hydroxytryptophan: An unusual amino acid residue from the cyclic hexapeptide keramamide A
    • (c) Zhang P, Liu R, Cook JM. (1995) An enantiospecific synthesis of L(-) and D(+)-6-Chloro-5-hydroxytryptophan: An unusual amino acid residue from the cyclic hexapeptide keramamide A. Tetrahedron Letters, 36, 7411-7414.
    • (1995) Tetrahedron Letters , vol.36 , pp. 7411-7414
    • Zhang, P.1    Liu, R.2    Cook, J.M.3
  • 128
    • 0026769197 scopus 로고
    • Entry into 6-methoxy-D-(+)-tryptophans. Stereospecific synthesis of 1-benzenesulfonyl-6-methoxy-D(+)-tryptophan ethyl ester
    • Allen MS, Hamaker LK, LaLoggia AS, Cook JM. (1992) Entry into 6-methoxy-D-(+)-tryptophans. Stereospecific synthesis of 1-benzenesulfonyl-6- methoxy-D(+)-tryptophan ethyl ester. Synthetic Communications, 22, 2077-2102.
    • (1992) Synthetic Communications , vol.22 , pp. 2077-2102
    • Allen, M.S.1    Hamaker, L.K.2    LaLoggia, A.S.3    Cook, J.M.4
  • 129
    • 0028805603 scopus 로고
    • Enantiospecific synthesis of 5-methoxy-D(+)- Or L(-)tryptophan
    • Zhang P, Cook JM. (1995) Enantiospecific synthesis of 5-methoxy-D(+)- or L(-)tryptophan. Synthetic Communications, 25, 3883-3900.
    • (1995) Synthetic Communications , vol.25 , pp. 3883-3900
    • Zhang, P.1    Cook, J.M.2
  • 130
    • 0000479568 scopus 로고    scopus 로고
    • Synthesis of isoquinolines and pyridines by the palladium- And copper-catalyzed coupling and cyclization of terminal acetylenes
    • (a) Roesch KR, Larock RC (1999) Synthesis of isoquinolines and pyridines by the palladium- and copper-catalyzed coupling and cyclization of terminal acetylenes. Organic Letters, 1, 553-556.
    • (1999) Organic Letters , vol.1 , pp. 553-556
    • Roesch, K.R.1    Larock, R.C.2
  • 131
    • 0029042650 scopus 로고
    • Synthesis of aromatic heterocycles via palladium-catalyzed annulation of internal alkynes
    • (b) Larock RC, Yum EK, Doty MJ, Sham KelvinKC. (1995) Synthesis of aromatic heterocycles via palladium-catalyzed annulation of internal alkynes. The Journal of Organic Chemistry, 60, 3270-3271.
    • (1995) The Journal of Organic Chemistry , vol.60 , pp. 3270-3271
    • Larock, R.C.1    Yum, E.K.2    Doty, M.J.3    Sham Kelvin, K.C.4
  • 132
    • 0000913941 scopus 로고
    • Synthesis of indenones via palladium-catalyzed annulation of internal alkynes
    • (c) Larock RC, Doty MJ, Cacchi S. (1993) Synthesis of indenones via palladium-catalyzed annulation of internal alkynes. The Journal of Organic Chemistry, 58, 4579-4583.
    • (1993) The Journal of Organic Chemistry , vol.58 , pp. 4579-4583
    • Larock, R.C.1    Doty, M.J.2    Cacchi, S.3
  • 133
    • 0034655465 scopus 로고    scopus 로고
    • Efficient asymmetric synthesis of important tryptophan analogues for biological research via the Schöllkopf chiral auxiliary
    • (a) Ma C, Yu S, He X, Liu X, Cook JM. (2000) Efficient asymmetric synthesis of important tryptophan analogues for biological research via the Schöllkopf chiral auxiliary. Tetrahedron Letters, 41, 2781-2785.
    • (2000) Tetrahedron Letters , vol.41 , pp. 2781-2785
    • Ma, C.1    Yu, S.2    He, X.3    Liu, X.4    Cook, J.M.5
  • 134
    • 0035967767 scopus 로고    scopus 로고
    • Efficient asymmetric synthesis of biologically important tryptophan analogues via a palladium-mediated heteroannulation reaction
    • (b) Ma C, Liu X, Li X, Flippen-Anderson J, Yu S, Cook JM. (2001) Efficient asymmetric synthesis of biologically important tryptophan analogues via a palladium-mediated heteroannulation reaction. The Journal of Organic Chemistry, 66, 4525-4542.
    • (2001) The Journal of Organic Chemistry , vol.66 , pp. 4525-4542
    • Ma, C.1    Liu, X.2    Li, X.3    Flippen-Anderson, J.4    Yu, S.5    Cook, J.M.6
  • 138
    • 0026620170 scopus 로고
    • Iodination of aromatic amines with iodine and silver sulfate
    • (a) Sy WW. (1992) Iodination of aromatic amines with iodine and silver sulfate. Synthetic Communications, 22, 3215-3219.
    • (1992) Synthetic Communications , vol.22 , pp. 3215-3219
    • Sy, W.W.1
  • 140
    • 0030816416 scopus 로고    scopus 로고
    • General and facile synthesis of indoles with oxygen-bearing substituents at the benzene moiety
    • (c) Kondo Y, Kojima S, Sakamoto, T. (1997) General and facile synthesis of indoles with oxygen-bearing substituents at the benzene moiety. The Journal of Organic Chemistry, 62, 6507-6511.
    • (1997) The Journal of Organic Chemistry , vol.62 , pp. 6507-6511
    • Kondo, Y.1    Kojima, S.2    Sakamoto, T.3
  • 141
    • 0035930743 scopus 로고    scopus 로고
    • A novel and economical route to (±)-horsfiline using an aryl iodoazide tandem radical cyclisation strategy
    • Lizos D, Tripoli R, Murphy JA. (2001) A novel and economical route to (±)-horsfiline using an aryl iodoazide tandem radical cyclisation strategy. Chemical Communications, 24, 2732-2733.
    • (2001) Chemical Communications , vol.24 , pp. 2732-2733
    • Lizos, D.1    Tripoli, R.2    Murphy, J.A.3
  • 142
    • 0842306887 scopus 로고    scopus 로고
    • a- methylvellosimine, (+)-12-methoxyaffinisine, and (-)-fuchsiaefoline
    • a-methylvellosimine, (+)-12-methoxyaffinisine, and (-)-fuchsiaefoline. Organic Letters, 6, 249-252.
    • (2004) Organic Letters , vol.6 , pp. 249-252
    • Zhou, H.1    Liao, X.2    Cook, J.M.3
  • 144
    • 0343391102 scopus 로고    scopus 로고
    • General approach for the synthesis of indole alkaloids via the asymmetric Pictet-Spengler reaction: First enantiospecific total synthesis of (-)-corynantheidine as well as the enantiospecific total synthesis of (-)-corynanthediol, (-)-geissoschizol and (+)-geissoschizine
    • (a) Yu S, Berner OM, Cook JM. (2000) General approach for the synthesis of indole alkaloids via the asymmetric Pictet-Spengler reaction: First enantiospecific total synthesis of (-)-corynantheidine as well as the enantiospecific total synthesis of (-)-corynanthediol, (-)-geissoschizol and (+)-geissoschizine. Journal of the American Chemical Society, 122, 7827-7828.
    • (2000) Journal of the American Chemical Society , vol.122 , pp. 7827-7828
    • Yu, S.1    Berner, O.M.2    Cook, J.M.3
  • 147
    • 0002500161 scopus 로고
    • Tryptamines, carbolines, and related compounds. II. A convenient synthesis of tryptamines and β- Carbolines
    • Abramovitch RA, Shapiro DS. (1956) Tryptamines, carbolines, and related compounds. II. A convenient synthesis of tryptamines and β- carbolines. Journal of the Chemical Society, 1, 4589-4592.
    • (1956) Journal of the Chemical Society , vol.1 , pp. 4589-4592
    • Abramovitch, R.A.1    Shapiro, D.S.2
  • 148
    • 0037035041 scopus 로고    scopus 로고
    • a-methylsarpagine as well as the total synthesis of the Alstonia bisindole macralstonidine
    • a-methylsarpagine as well as the total synthesis of the Alstonia bisindole macralstonidine. Organic Letters, 4, 687-690.
    • (2002) Organic Letters , vol.4 , pp. 687-690
    • Zhao, S.1    Liao, X.2    Cook, J.M.3
  • 151
    • 0037015424 scopus 로고    scopus 로고
    • a-methygardneral, 11-methoxyaffinisine, and 11-methoxymacroline as well as the indole alkaloids alstophylline and macralstonine
    • a-methygardneral, 11-methoxyaffinisine, and 11-methoxymacroline as well as the indole alkaloids alstophylline and macralstonine. Organic Letters, 4, 3339-3342.
    • (2002) Organic Letters , vol.4 , pp. 3339-3342
    • Liu, X.1    Cook, J.M.2
  • 153
    • 0038272218 scopus 로고    scopus 로고
    • Stereospecific enantiospecific total synthesis of the sarpagine indole alkaloids (E)16-epiaffinisine, (E)16-epinormacusine B and dehydro-16- epiaffinisine
    • (a) Yu J, Liao X, Cook JM. (2002) Stereospecific enantiospecific total synthesis of the sarpagine indole alkaloids (E)16-epiaffinisine, (E)16-epinormacusine B and dehydro-16-epiaffinisine. Organic Letters, 4, 4681-4684.
    • (2002) Organic Letters , vol.4 , pp. 4681-4684
    • Yu, J.1    Liao, X.2    Cook, J.M.3
  • 154
    • 0038034867 scopus 로고    scopus 로고
    • Enantiospecific total synthesis of (-)-(E)16-epiaffinisine, (+)-(E)16-epinormacusine B, and (+)- Dehydro- 16-epiaffinisine as well as the stereocontrolled total synthesis of alkaloid G
    • (b) Yu J, Wang T, Wearing X, Ma J, Cook JM. (2003) Enantiospecific total synthesis of (-)-(E)16-epiaffinisine, (+)-(E)16-epinormacusine B, and (+)- dehydro- 16-epiaffinisine as well as the stereocontrolled total synthesis of alkaloid G. The Journal of Organic Chemistry, 68, 5852-5859.
    • (2003) The Journal of Organic Chemistry , vol.68 , pp. 5852-5859
    • Yu, J.1    Wang, T.2    Wearing, X.3    Ma, J.4    Cook, J.M.5
  • 155
    • 19044364997 scopus 로고    scopus 로고
    • First regiospecific, enantiospecific total synthesis of gardnerine and gardnutine
    • (c) Zhou H, Han D, Liao X, Cook JM. (2005) First regiospecific, enantiospecific total synthesis of gardnerine and gardnutine. Tetrahedron Letters, 46, 4219-4224.
    • (2005) Tetrahedron Letters , vol.46 , pp. 4219-4224
    • Zhou, H.1    Han, D.2    Liao, X.3    Cook, J.M.4
  • 156
    • 77954186196 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of Wisconsin-Milwaukee
    • A/benzodiazepine receptor subtypes: SAR studies of β-carbolines at position-3 and -6 and their corresponding bivalent ligands. Part III. First enantiospecific total synthesis of the important biogenetic intermediates, (+)-polyneuridine aldehyde, as well as 16-epi-vellosimine and macusine A. Ph.D. Thesis, University of Wisconsin-Milwaukee.
    • (2007) A
    • Yin, W.1
  • 157
    • 33846623329 scopus 로고    scopus 로고
    • First enantiospecific total synthesis of the important biogenetic intermediates, (+)-polyneuridine and (+)-polyneuridine aldehyde, as well as 16-epi-vellosimine and macusine-A
    • (b) Yin W, Ma J, Rivas FM, Cook JM. (2007) First enantiospecific total synthesis of the important biogenetic intermediates, (+)-polyneuridine and (+)-polyneuridine aldehyde, as well as 16-epi-vellosimine and macusine-A. Organic Letters, 9, 295-298.
    • (2007) Organic Letters , vol.9 , pp. 295-298
    • Yin, W.1    Ma, J.2    Rivas, F.M.3    Cook, J.M.4
  • 158
    • 0000325856 scopus 로고
    • Silane reductions in acidic media. II. Reductions of aryl aldehydes and ketones by trialkylsilanes in trifluoroacetic acid. Selective method for converting the carbonyl group to methylene
    • West CT, Donnelly SJ, Kooistra DA, Doyle MP. (1973) Silane reductions in acidic media. II. Reductions of aryl aldehydes and ketones by trialkylsilanes in trifluoroacetic acid. Selective method for converting the carbonyl group to methylene. The Journal of Organic Chemistry, 38, 2675-2681.
    • (1973) The Journal of Organic Chemistry , vol.38 , pp. 2675-2681
    • West, C.T.1    Donnelly, S.J.2    Kooistra, D.A.3    Doyle, M.P.4
  • 162
    • 1942504309 scopus 로고    scopus 로고
    • The first enantiospecific total synthesis of a C-quaternary voachalotine alkaloid, (+)-dehydrovoachalotine
    • Yu J, Wearing XZ, Cook JM. (2004) The first enantiospecific total synthesis of a C-quaternary voachalotine alkaloid, (+)-dehydrovoachalotine. Tetrahedron Letters, 45, 3937-3940.
    • (2004) Tetrahedron Letters , vol.45 , pp. 3937-3940
    • Yu, J.1    Wearing, X.Z.2    Cook, J.M.3
  • 163
    • 1042265069 scopus 로고    scopus 로고
    • Stereocontrolled total synthesis of (-)-vincamajinine and (-)-11-methoxy-17-epivincamajine
    • (a) Yu J, Wearing XZ, Cook JM. (2004) Stereocontrolled total synthesis of (-)-vincamajinine and (-)-11-methoxy-17-epivincamajine. Journal of the American Chemical Society, 126, 1358-1359.
    • (2004) Journal of the American Chemical Society , vol.126 , pp. 1358-1359
    • Yu, J.1    Wearing, X.Z.2    Cook, J.M.3
  • 164
    • 18744399313 scopus 로고    scopus 로고
    • A general strategy for the synthesis of vincamajine-related indole alkaloids: Stereocontrolled total synthesis of (+)-dehydrovoachalotine, (-)-vincamajinine, and (-)-11-methoxy-17-epivincamajine as well as the related quebrachidine diol, vincamajine diol and vincarinol
    • (b) Yu J, Wearing A, Cook JM. (2005) A general strategy for the synthesis of vincamajine-related indole alkaloids: Stereocontrolled total synthesis of (+)-dehydrovoachalotine, (-)-vincamajinine, and (-)-11-methoxy-17-epivincamajine as well as the related quebrachidine diol, vincamajine diol and vincarinol. The Journal of Organic Chemistry, 70, 3963-3979.
    • (2005) The Journal of Organic Chemistry , vol.70 , pp. 3963-3979
    • Yu, J.1    Wearing, A.2    Cook, J.M.3
  • 167
    • 77954179770 scopus 로고    scopus 로고
    • 2O/HCl(g)/AcOH was reported in the total synthesis of ajmaline-related alkaloids; see: ref 25a. This condition did not work in this case even after stirring for 5 days
    • 2O/HCl(g)/AcOH was reported in the total synthesis of ajmaline-related alkaloids; see: ref 25a. This condition did not work in this case even after stirring for 5 days.
  • 168
    • 23944503767 scopus 로고    scopus 로고
    • The first regiospecific, enantiospecific total synthesis of 6- Oxoalstophylline and an improved total synthesis of alstonerine and alstophylline as well as the bisindole alkaloid macralstonine
    • Liao X, Zhou H, Wearing XZ, Ma J, Cook JM. (2005) The first regiospecific, enantiospecific total synthesis of 6- oxoalstophylline and an improved total synthesis of alstonerine and alstophylline as well as the bisindole alkaloid macralstonine. Organic Letters, 7, 3501-3504.
    • (2005) Organic Letters , vol.7 , pp. 3501-3504
    • Liao, X.1    Zhou, H.2    Wearing, X.Z.3    Ma, J.4    Cook, J.M.5
  • 169
    • 0003092156 scopus 로고
    • A new preparative method for 1, 3-dicarbonyl compounds by the regioselective oxidation of □□-unsaturated carbonyl compounds catalyzed by palladium(II) chloride using hydroperoxides as the reoxidant of palladium(0)
    • Tsuji J, Nagashima H, Hori K. (1980) A new preparative method for 1, 3-dicarbonyl compounds by the regioselective oxidation of □□-unsaturated carbonyl compounds catalyzed by palladium(II) chloride using hydroperoxides as the reoxidant of palladium(0). Chemisty Letters, 3, 257-260.
    • (1980) Chemisty Letters , vol.3 , pp. 257-260
    • Tsuji, J.1    Nagashima, H.2    Hori, K.3
  • 170
    • 0742269535 scopus 로고    scopus 로고
    • Oxidative cyclization of β-hydroxyenones with palladium(II): A novel entry to 2,3-dihydro-4H-pyran-4-ones
    • (a) Reiter M, Ropp S, Gouverneur V. (2004) Oxidative cyclization of β-hydroxyenones with palladium(II): A novel entry to 2,3-dihydro-4H-pyran- 4-ones. Organic Letters, 6, 91-94.
    • (2004) Organic Letters , vol.6 , pp. 91-94
    • Reiter, M.1    Ropp, S.2    Gouverneur, V.3
  • 171
    • 0000300355 scopus 로고
    • Palladium(II)- Catalyzed acetalization of terminal olefins bearing electron-withdrawing substituents with optically active diols
    • (b) Hosokawa T, Ohta T, Kanayama S, Murahashi S. (1987) Palladium(II)- catalyzed acetalization of terminal olefins bearing electron-withdrawing substituents with optically active diols. The Journal of Organic Chemistry, 52, 1758-1764.
    • (1987) The Journal of Organic Chemistry , vol.52 , pp. 1758-1764
    • Hosokawa, T.1    Ohta, T.2    Kanayama, S.3    Murahashi, S.4
  • 172
    • 0141485280 scopus 로고    scopus 로고
    • The first enantiospecific synthesis of (-)-koumidine via the intramolecular palladium-catalyed enolate driven cross coupling reaction. The stereospecific introduction of the 19-(Z) ethylidene side chain
    • Cao H, Yu J, Wearing XZ, Zhang C, Lui X, Deschamps J, Cook JM. (2003) The first enantiospecific synthesis of (-)-koumidine via the intramolecular palladium-catalyed enolate driven cross coupling reaction. The stereospecific introduction of the 19-(Z) ethylidene side chain. Tetrahedron Letters, 44, 8013-8017.
    • (2003) Tetrahedron Letters , vol.44 , pp. 8013-8017
    • Cao, H.1    Yu, J.2    Wearing, X.Z.3    Zhang, C.4    Lui, X.5    Deschamps, J.6    Cook, J.M.7
  • 174
    • 33750864963 scopus 로고    scopus 로고
    • An improved total synthesis of (+)-macroline and alstonerine as well as the formal total synthesis of (-)- Talcarpine and (-)-anhydromacrosalhine- methine
    • Liao X, Zhou H, Yu J, Cook JM. (2006). An improved total synthesis of (+)-macroline and alstonerine as well as the formal total synthesis of (-)- talcarpine and (-)-anhydromacrosalhine-methine. The Journal of Organic Chemistry, 71, 8884-8890.
    • (2006) The Journal of Organic Chemistry , vol.71 , pp. 8884-8890
    • Liao, X.1    Zhou, H.2    Yu, J.3    Cook, J.M.4
  • 176
    • 34247470787 scopus 로고    scopus 로고
    • Cascade approach toward the core structure of neosarpagine
    • Liao X, Huang S, Zhou H, Parrish D, Cook JM. (2007) Cascade approach toward the core structure of neosarpagine. Organic Letters, 9, 1469-1471.
    • (2007) Organic Letters , vol.9 , pp. 1469-1471
    • Liao, X.1    Huang, S.2    Zhou, H.3    Parrish, D.4    Cook, J.M.5
  • 177
    • 0030860106 scopus 로고    scopus 로고
    • Highly efficient synthesis of cephalotaxine by two palladium-catalyzed cyclizations
    • Tietze LF, Schirok H. (1997) Highly efficient synthesis of cephalotaxine by two palladium-catalyzed cyclizations. Angewandte Chemie International Edition, 36, 1124-1125.
    • (1997) Angewandte Chemie International Edition , vol.36 , pp. 1124-1125
    • Tietze, L.F.1    Schirok, H.2
  • 178
    • 7044277371 scopus 로고
    • a-methyl-Δ18-isokoumidine, a possible precursor of the koumine type indole alkaloids
    • a-methyl-Δ18- isokoumidine, a possible precursor of the koumine type indole alkaloids. Tetrahedron Letters, 30, 3457-3460.
    • (1989) Tetrahedron Letters , vol.30 , pp. 3457-3460
    • Liu, Z.1    Xu, F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.