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Volumn 5, Issue 2, 2013, Pages 126-131

A divergent approach to the synthesis of the yohimbinoid alkaloids venenatine and alstovenine

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ALSTOVENINE; DRUG DERIVATIVE; TOLUENE; VENENATINE; YOHIMBINE;

EID: 84873858773     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.1528     Document Type: Article
Times cited : (54)

References (49)
  • 1
    • 30844451834 scopus 로고    scopus 로고
    • Reserpine: A challenge for total synthesis of natural products
    • Chen, F-E. & Huang, J. Reserpine: A challenge for total synthesis of natural products. Chem. Rev. 105, 4671-4706 (2005
    • (2005) Chem. Rev , vol.105 , pp. 4671-4706
    • Chen, F.-E.1    Huang, J.2
  • 5
  • 7
    • 0021054336 scopus 로고
    • Yohimbine: A pharmacological probe for study of the alpha-2- Adrenoreceptor
    • Goldberg, M. R. & Robertson D. Yohimbine: A pharmacological probe for study of the alpha-2-Adrenoreceptor. Pharmacological Reviews 35, 143-180 (1983
    • (1983) Pharmacological Reviews , vol.35 , pp. 143-180
    • Goldberg, M.R.1    Robertson, D.2
  • 11
    • 33947467261 scopus 로고
    • A simplified route to a key intermediate in the total synthesis of reserpine
    • Woodward, R. B., Bader, F. E., Bickel, H., Frey, A. J. & Kierstead, R. W. A simplified route to a key intermediate in the total synthesis of reserpine. J. Am. Chem. Soc. 78, 2657-2657 (1956
    • (1956) J. Am. Chem. Soc , vol.78 , pp. 2657-2657
    • Woodward, R.B.1    Bader, F.E.2    Bickel, H.3    Frey, A.J.4    Kierstead, R.W.5
  • 12
    • 0000999169 scopus 로고
    • The stereospecific synthesis of reserpine
    • Stork, G. The stereospecific synthesis of reserpine. Pure. Appl. Chem. 61, 439-442 (1989
    • (1989) Pure. Appl. Chem , vol.61 , pp. 439-442
    • Stork, G.1
  • 13
    • 28044452880 scopus 로고    scopus 로고
    • Regiospecific and stereoselective syntheses of (+)-reserpine and (2)-reserpine
    • Stork, G., Tang, P. C., Casey, M., Goodman, B. & Toyota, M. Regiospecific and stereoselective syntheses of (+)-reserpine and (2)-reserpine. J. Am. Chem. Soc. 127, 16255-16262 (2005
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 16255-16262
    • Stork, G.1    Tang, P.C.2    Casey, M.3    Goodman, B.4    Toyota, M.5
  • 14
    • 0019129927 scopus 로고
    • General methodology for cis-hydroisoquinoline syn thesis: Synthesis of reserpine
    • Wender, P. A., Schaus, J. M. & White, A. W. General methodology for cis-hydroisoquinoline synthesis: Synthesis of reserpine. J. Am. Chem. Soc. 102, 6157-6159 (1980
    • (1980) J. Am. Chem. Soc , vol.102 , pp. 6157-6159
    • Wender, P.A.1    Schaus, J.M.2    White, A.W.3
  • 15
    • 28044435882 scopus 로고
    • General methodology for cis-hydroisoquinoline synthesis 3 A sixteen step synthesis of reserpine
    • Wender, P. A., Schaus, J. M. & White, A. W. General methodology for cis-hydroisoquinoline synthesis. 3. A sixteen step synthesis of reserpine. Heterocycles 3, 263-270 (1987
    • (1987) Heterocycles , vol.3 , pp. 263-270
    • Wender, P.A.1    Schaus, J.M.2    White, A.W.3
  • 17
    • 0018639628 scopus 로고
    • Total synthesis of the yohimbines
    • Wenkert, E. et al. Total synthesis of the yohimbines. J. Am. Chem. Soc. 101, 5370-5376 (1979
    • (1979) J. Am. Chem. Soc , vol.101 , pp. 5370-5376
    • Wenkert, E.1
  • 18
    • 0037533940 scopus 로고    scopus 로고
    • Preparation of perhydroisoquinolines via the intramolecular Diels-Alder reaction of N-3,5-hexadienoyl ethyl acrylimidates: A formal synthesis of (+)-reserpine
    • Sparks, S. M., Gutierrez, A. J. & Shea, K. J. Preparation of perhydroisoquinolines via the intramolecular Diels-Alder reaction of N-3,5-hexadienoyl ethyl acrylimidates: A formal synthesis of (+)-reserpine. J. Org. Chem. 68, 5274-5285 (2003
    • (2003) J. Org. Chem , vol.68 , pp. 5274-5285
    • Sparks, S.M.1    Gutierrez, A.J.2    Shea, K.J.3
  • 19
    • 0017117505 scopus 로고
    • Über eine einfache synthese der yohimbinalkaloide
    • Szantay, C., Honty, K., Toke, L. & Szabo, L. ü ber Eine Einfache Synthese der Yohimbinalkaloide. Chem. Ber. 109, 1737-1748 (1976
    • (1976) Chem. Ber , vol.109 , pp. 1737-1748
    • Szantay, C.1    Honty, K.2    Toke, L.3    Szabo, L.4
  • 20
    • 0015794740 scopus 로고
    • Synthesis of yohimbines I Total synthesis of alloyohimbine and a-yohimbine and their epimers Revised structure of natural alloyohimbine
    • Toke, L., Honty, K., Szabo, L., Blasko, G. & Szantay, C. Synthesis of yohimbines. I. Total synthesis of alloyohimbine and a-yohimbine and their epimers. Revised structure of natural alloyohimbine. J. Org. Chem. 38, 2496-2500 (1973
    • (1973) J. Org. Chem , vol.38 , pp. 2496-2500
    • Toke, L.1    Honty, K.2    Szabo, L.3    Blasko, G.4    Szantay, C.5
  • 23
    • 84873823268 scopus 로고
    • The alkaloids of rauwolfia canescens linn II
    • Mookerjee, A. The alkaloids of Rauwolfia canescens linn. II. J. Ind. Chem. Soc. 485-488 (1941
    • (1941) J Ind. Chem. Soc , pp. 485-488
    • Mookerjee, A.1
  • 24
    • 85027471500 scopus 로고
    • Uber zwei neue alkaloide aus der yohimberinde
    • Karrer, P. & Salomon, H. Uber Zwei Neue Alkaloide aus der Yohimberinde. Helv. Chim. Acta 9, 1059-1062 (1926
    • (1926) Helv. Chim. Acta , vol.9 , pp. 1059-1062
    • Karrer, P.1    Salomon, H.2
  • 25
    • 34548683032 scopus 로고
    • Alkaloids of aspidosperma excelsum benth
    • Benoin, P. R., Burnell, R. H. & Medina, J. D. Alkaloids of Aspidosperma excelsum Benth. Can. J. Chem. 45, 725-730 (1967
    • (1967) Can. J. Chem , vol.45 , pp. 725-730
    • Benoin, P.R.1    Burnell, R.H.2    Medina, J.D.3
  • 26
    • 4544338819 scopus 로고    scopus 로고
    • A new 9-methoxyyohimbine-Type indole alkaloid from Mitragyna africanus
    • Takayama, H., Ishikawa, H., Kitajima, M., Aimi, N. & Aji, B. M. A new 9-methoxyyohimbine-Type indole alkaloid from Mitragyna africanus. Chem. Pharm. Bull. 52, 359-361 (2004
    • (2004) Chem. Pharm. Bull , vol.52 , pp. 359-361
    • Takayama, H.1    Ishikawa, H.2    Kitajima, M.3    Aimi, N.4    Aji, B.M.5
  • 27
    • 50549218928 scopus 로고
    • Structure of venoxidine, an alkaloid of Alstonia venenata R
    • Chatterjee, A., Majumder, P. L. & Ray, A. B. Structure of venoxidine, an alkaloid of Alstonia venenata R. Br. Tetrahedron Lett. 42, 159-162 (1965
    • (1965) Br. Tetrahedron Lett , vol.42 , pp. 159-162
    • Chatterjee, A.1    Majumder, P.L.2    Ray, A.B.3
  • 30
    • 49149135666 scopus 로고
    • 16-epivenenatine and 16-epialstovenine, new stereomers from Alstonia venenata
    • Chatterjee, A., Roy, D. J. & Mukhopadhyay, S. 16-epivenenatine and 16-epialstovenine, new stereomers from Alstonia venenata. Phytochemistry 20, 1981-1985 (1981
    • (1981) Phytochemistry , vol.20 , pp. 1981-1985
    • Chatterjee, A.1    Roy, D.J.2    Mukhopadhyay, S.3
  • 31
    • 84873876640 scopus 로고
    • Alstovenine a new indole alkaloid isolated from Alstonia venenatus R
    • Ray, A. B. & Chatterjee, A. Alstovenine, a new indole alkaloid isolated from Alstonia venenatus R. Br. J. Indian Chem. Soc. 40, 1043-1044 (1963
    • (1963) Br. J. Indian Chem. Soc , vol.40 , pp. 1043-1044
    • Ray, A.B.1    Chatterjee, A.2
  • 32
    • 84873809297 scopus 로고
    • Root alkaloids of Alstonia venenata R
    • Dutta, S. C. & Ray, A. B. Root alkaloids of Alstonia venenata R. Br. Indian. J. Chem. 13, 98-100 (1975
    • (1975) Br. Indian. J. Chem , vol.13 , pp. 98-100
    • Dutta, S.C.1    Ray, A.B.2
  • 33
    • 0041789619 scopus 로고
    • Further studies on the major alkaloids of the stem-bark of alstonia venenata r br structure and stereochemistry of alstovenine and its congeners
    • Ray, A. B. & Chatterjee, A. Further studies on the major alkaloids of the stem-bark of Alstonia venenata R. Br. Structure and stereochemistry of alstovenine and its congeners. J. Indian Chem. Soc. 41, 638-640 (1964
    • (1964) J. Indian Chem. Soc , vol.41 , pp. 638-640
    • Ray, A.B.1    Chatterjee, A.2
  • 34
    • 0016635838 scopus 로고
    • Psychopharmacological investigations of the 4-methoxyindole alkaloids of Alstonia venenata
    • Bhattacharya, S. K., Ray, A. B. & Dutta, S. C. Psychopharmacological investigations of the 4-methoxyindole alkaloids of Alstonia venenata. Planta Med. 2, 164-170 (1975
    • (1975) Planta Med , vol.2 , pp. 164-170
    • Bhattacharya, S.K.1    Ray, A.B.2    Dutta, S.C.3
  • 35
    • 0023185656 scopus 로고
    • Berbanes: A new class of selective a-2-Adrenoceptor antagonists
    • Vizi, E. S. et al. Berbanes: A new class of selective a-2-Adrenoceptor antagonists. J. Med. Chem. 30, 1355-1359 (1987
    • (1987) J. Med. Chem , vol.30 , pp. 1355-1359
    • Vizi, E.S.1
  • 36
    • 0022485687 scopus 로고
    • CH-38083, a selective, potent antagonist of alpha-2 adrenoceptors
    • Vizi, E. S. et al. CH-38083, a selective, potent antagonist of alpha-2 adrenoceptors. J. Pharmacol. Exp. Ther. 238, 701-706 (1986
    • (1986) J. Pharmacol. Exp. Ther , vol.238 , pp. 701-706
    • Vizi, E.S.1
  • 37
    • 0021703493 scopus 로고
    • Investigations on the chemistry of berbanes 10 Synthesis of raunescinone analogs with hypotensive and antihypertensive activity
    • Toth, I. et al. Investigations on the chemistry of berbanes. 10. Synthesis of raunescinone analogs with hypotensive and antihypertensive activity. J. Med. Chem. 27, 1411-1415 (1984
    • (1984) J. Med. Chem , vol.27 , pp. 1411-1415
    • Toth, I.1
  • 38
    • 0021691018 scopus 로고
    • Stereospecific synthesis of substituted cis-hydrindan-5-one and their regiospecific enolization and functionalization: Synthetic intermediates for reserpine
    • Jung, M. E. & Light, L. A. Stereospecific synthesis of substituted cis-hydrindan-5-one and their regiospecific enolization and functionalization: Synthetic intermediates for reserpine. J. Am. Chem. Soc. 106, 7614-7618 (1984
    • (1984) J. Am. Chem. Soc , vol.106 , pp. 7614-7618
    • Jung, M.E.1    Light, L.A.2
  • 39
    • 0020677879 scopus 로고
    • Synthese stereoselective des cis et trans carboxy-4-Tetrahydro-3a,4 ,5,6-indanones-1
    • Ficini, J., Guingant, A. & d'Angelo, J. Synthese stereoselective des cis et trans carboxy-4-Tetrahydro-3a,4,5,6-indanones-1. Tetrahedron Lett. 24, 907-910 (1983
    • (1983) Tetrahedron Lett , vol.24 , pp. 907-910
    • Ficini, J.1    Guingant, A.2    D'angelo, J.3
  • 40
    • 84860114638 scopus 로고    scopus 로고
    • Synthesis of the bridging framework of phragmalin-Type limonoids
    • Lebold, T. P., Gallego, G. M., Marth, C. J. & Sarpong, R. Synthesis of the bridging framework of phragmalin-Type limonoids. Org. Lett. 14, 2110-2113 (2012
    • (2012) Org. Lett , vol.14 , pp. 2110-2113
    • Lebold, T.P.1    Gallego, G.M.2    Marth, C.J.3    Sarpong, R.4
  • 41
    • 0022406076 scopus 로고
    • Total synthesis of the sesquiterpene (+)-hirsutene using an organoselenium-mediated cyclization reaction
    • Ley, S. V., Murray, P. J. & Palmer, B. D. Total synthesis of the sesquiterpene (+)-hirsutene using an organoselenium-mediated cyclization reaction. Tetrahedron 41, 4765-4769 (1985
    • (1985) Tetrahedron , vol.41 , pp. 4765-4769
    • Ley, S.V.1    Murray, P.J.2    Palmer, B.D.3
  • 42
    • 33646767009 scopus 로고    scopus 로고
    • Ortep-3 for Windows - A version of ORTEP-III with a graphical user interface (GUI
    • Farrugia, L. J. Ortep-3 for Windows - A version of ORTEP-III with a graphical user interface (GUI). J. Appl. Crystallogr. 30, 565-566 (1997
    • (1997) J. Appl. Crystallogr , vol.30 , pp. 565-566
    • Farrugia, L.J.1
  • 43
    • 34547325807 scopus 로고    scopus 로고
    • Nucleophilicity of indole derivatives: Activating and deactivating effects based on proton affinities and electron density properties
    • Otero, N., Mandado, M. & Mosquera, R. A. Nucleophilicity of indole derivatives: Activating and deactivating effects based on proton affinities and electron density properties. J. Phys. Chem. A. 111, 5557-5562 (2007
    • (2007) J. Phys. Chem. A. , vol.111 , pp. 5557-5562
    • Otero, N.1    Mandado, M.2    Mosquera, R.A.3
  • 44
    • 77955144553 scopus 로고    scopus 로고
    • Nucleophilicity and site selectivity of commonly used arenes and heteroarenes
    • Pratihar, S. & Roy, S. Nucleophilicity and site selectivity of commonly used arenes and heteroarenes. J. Org. Chem. 75, 4957-4963 (2010
    • (2010) J. Org. Chem , vol.75 , pp. 4957-4963
    • Pratihar, S.1    Roy, S.2
  • 45
    • 33847061595 scopus 로고    scopus 로고
    • Conformational analysis of the cis- And trans-Adducts of the Pictet-Spengler reaction Evidence for the structural basis for the C (1)-N(2) scission process in the cis- To trans-isomerization
    • Han, D. et al. Conformational analysis of the cis- And trans-Adducts of the Pictet-Spengler reaction. Evidence for the structural basis for the C(1)-N(2) scission process in the cis- To trans-isomerization. J. Nat. Prod. 70, 75-82 (2007
    • (2007) J Nat Prod , vol.70 , pp. 75-82
    • Han, D.1
  • 46
    • 0026088617 scopus 로고
    • Stereospecificity in the Pictet-Spengler reaction kinetic vs thermodynamic control
    • Deng, L., Czerwinski, K. & Cook, J. M. Stereospecificity in the Pictet-Spengler reaction kinetic vs thermodynamic control. Tetrahedron Lett. 32, 175-178 (1991
    • (1991) Tetrahedron Lett , vol.32 , pp. 175-178
    • Deng, L.1    Czerwinski, K.2    Cook, J.M.3
  • 47
    • 0000909909 scopus 로고
    • Stereoregulation of the C(12b)H-C(2)H relationship in the preparation of 2-substituted 1 2 34671212b-octahydroindolo[ 23-A]quinolizines
    • Lounasmaa, M. & Jokela, R. Stereoregulation of the C(12b)H-C(2)H relationship in the preparation of 2-substituted 1,2,3,4,6,7,12,12b- octahydroindolo[ 2,3-A]quinolizines. Tetrahedron 45, 3975-3992 (1989
    • (1989) Tetrahedron , vol.45 , pp. 3975-3992
    • Lounasmaa, M.1    Jokela, R.2
  • 49
    • 84856301655 scopus 로고    scopus 로고
    • Computational prediction of 1H and 13C chemical shifts: A useful tool for natural product, mechanistic, and synthetic organic chemistry
    • Lodewyk, M. W., Siebert, M. R. & Tantillo, D. J. Computational prediction of 1H and 13C chemical shifts: A useful tool for natural product, mechanistic, and synthetic organic chemistry. Chem. Rev. 112, 1839-1862 (2012
    • (2012) Chem. Rev , vol.112 , pp. 1839-1862
    • Lodewyk, M.W.1    Siebert, M.R.2    Tantillo, D.J.3


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