Synthesis of Bis-Strychnos Alkaloids (–)-Sungucine, (–)-Isosungucine, and (–)-Strychnogucine B from (–)-Strychnine

It was developed a concise synthetic route resulting in the first syntheses of bis-Strychnos alkaloids (-)-sungucine, (-)-isosungucine, and (-)-strychnogucine B from commercially available (-)-strychnine. Employing a highly convergent synthetic strategy, it was demonstrated that both Strychnos monom...

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Published inJournal of the Brazilian Chemical Society Vol. 30; no. 3; pp. 436 - 453
Main Authors Zhao, Senzhi, Teijaro, Christiana, Chen, Heng, Sirasani, Gopal, Vaddypally, Shivaiah, O’Sullivan, Owen, Zdilla, Michael, Dobereiner, Graham, Andrade, Rodrigo
Format Journal Article
LanguageEnglish
Published Sociedade Brasileira de Química 01.03.2019
Subjects
CHEMISTRY, MULTIDISCIPLINARY
sungucine
bis-Strychnos alkaloids
biomimetic synthesis
Mannich
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Abstract It was developed a concise synthetic route resulting in the first syntheses of bis-Strychnos alkaloids (-)-sungucine, (-)-isosungucine, and (-)-strychnogucine B from commercially available (-)-strychnine. Employing a highly convergent synthetic strategy, it was demonstrated that both Strychnos monomers could be efficiently prepared from commercially available (-)-strychnine. The venerable Mannich reaction was enlisted to join the two Strychnos monomers in a biomimetic fashion. Subsequent epimerization and olefin isomerization yielded (-)-strychnogucine B. Functional group manipulation transformed (-)-strychnogucine B into (-)-sungucine and (-)-isosungucine. Computational chemistry was employed to rationalize the regiochemical course of key steps en route to the bis-Strychnos targets.
AbstractList It was developed a concise synthetic route resulting in the first syntheses of bis-Strychnos alkaloids (-)-sungucine, (-)-isosungucine, and (-)-strychnogucine B from commercially available (-)-strychnine. Employing a highly convergent synthetic strategy, it was demonstrated that both Strychnos monomers could be efficiently prepared from commercially available (-)-strychnine. The venerable Mannich reaction was enlisted to join the two Strychnos monomers in a biomimetic fashion. Subsequent epimerization and olefin isomerization yielded (-)-strychnogucine B. Functional group manipulation transformed (-)-strychnogucine B into (-)-sungucine and (-)-isosungucine. Computational chemistry was employed to rationalize the regiochemical course of key steps en route to the bis-Strychnos targets.
Author Teijaro, Christiana
Vaddypally, Shivaiah
Sirasani, Gopal
Zhao, Senzhi
O’Sullivan, Owen
Dobereiner, Graham
Andrade, Rodrigo
Chen, Heng
Zdilla, Michael
AuthorAffiliation Temple University
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  surname: Andrade
  fullname: Andrade, Rodrigo
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Issue 3
Keywords sungucine
bis-Strychnos alkaloids
biomimetic synthesis
Mannich
Language English
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References Oesterlin, M.; Imoudsky, G. 1943; 76
Nicolaou, K. C.; Hwang, C. K.; Smith, A. L.; Wendeborn, S. V. 1990; 112
Still, W. C.; Kahn, M.; Mitra, A. 1978; 43
Kambu, K.; Coune, C.; Angenot, L. 1979; 37
Polonovski, M.; Polonovski, M. 1727; 41
Zhao, S.; Teijaro, C. N.; Chen, H.; Sirasani, G.; Vaddypally, S.; Zdilla, M. J.; Dobereiner, G. E.; Andrade, R. B. 2016; 22
Nishimoto, Y.; Yasuda, M.; Baba, A. 2007; 9
Heathcock, C. H.; Henderson, M. A.; Oare, D. A.; Sanner, M. A. 1985; 50
Shono, T.; Matsumura, Y.; Inoue, K.; Ohmizu, H.; Kashimura, S. 1982; 104
Lau, P. W. K.; Chan, T. H. 1978; 19
Teijaro, C. N.; Munagala, S.; Zhao, S.; Sirasani, G.; Kokkonda, P.; Malofeeva, E. V.; Hopper-Borge, E.; Andrade, R. B. 2014; 57
Wenkert, E.; Sklar, R. 1966; 31
Jung, M. E.; Usui, Y.; Vu, C. T. 1987; 28
Deiters, A.; Chen, K.; Eary, C. T.; Martin, S. F. 2003; 125
Frédérich, M.; Jacquier, M. J.; Thepenier, P.; De Mol, P.; Tits, M.; Philippe, G.; Delaude, C.; Angenot, L.; Zeches-Hanrot, M. 2002; 65
Evans, D. A.; Gage, J. R.; Leighton, J. L. 1992; 114
Frederich, M.; Bentires-Ali, M.; Tits, M.; Angenot, L.; Heinen, E.; De Pauw-Gillet, M. C. 2003; 367
Reed, A. E.; Weinstock, R. B.; Weinhold, F. 1985; 83
Kim, H. J.; Su, L.; Jung, H.; Koo, S. 2011; 13
Frédérich, M.; De Pauw, M.-C.; Prosperi, C.; Tits, M.; Brandt, V.; Penelle, J.; Hayette, M.-P.; De Mol, P.; Angenot, L. 2001; 64
Lansiaux, A.; Bailly, C.; Houssier, C.; Colson, P.; De Pauw-Gillet, M. C.; Frédérich, M.; Tits, M.; Angenot, L. 2002; 68
Overman, L. E.; Lesuisse, D.; Hashimoto, M. 1983; 105
Kogure, N.; Suzuki, Y.; Wu, Y.; Kitajima, M.; Zhang, R.; Takayama, H. 2012; 53
Frederich, M.; Tits, M.; Angenot, L. 2003; 39
McLeod, M. C.; Wilson, Z. E.; Brimble, M. A. 2012; 77
Fernandes, L.; Bortoluzzi, A. J.; Sá, M. M. 2004; 60
Utsugi, M.; Miyano, M.; Nakada, M. 2006; 8
Sirasani, G.; Andrade, R. B. 2009; 11
Suzuki, M.; Yanagisawa, A.; Noyori, R. 1982; 23
Sandberg, F.; Roos, K.; Ryrberg, K. J.; Kristiansson, K. 1968; 9
Leuchs, H.; Nitschke, R. 1922; 55
Litinskii, A. O.; Gokhberg, P. Y.; Shatkovskaya, D. B.; Bolotin, A. B.; Litinskaya, N. N.; Popov, G. P. 1984; 19
Kuehne, M. E.; Wang, T.; Seraphin, D. 1996; 61
Tsuji, J.; Mandai, T. 1996; 1996
Schümperli, M. T.; Hammond, C.; Hermans, I. 2012; 2
Grierson, D. S.; Harris, M.; Husson, H. P. 1980; 102
Keinan, E.; Greenspoon, N. 1982; 23
Frédérich, M.; De Pauw, M.-C.; Llabrès, G.; Tits, M.; Hayette, M.-P.; Brandt, V.; Penelle, J.; De Mol, P.; Angenot, L. 2000; 66
Oisaki, K.; Zhao, D.; Kanai, M.; Shibasaki, M. 2006; 128
Boit, H.-G. 1951; 84
Noble, A.; Anderson, J. C. 2013; 113
Zhao, S.; Andrade, R. B. 2013; 135
Tafel, J. 1898; 301
Ahond, A.; Cave, A.; Kan-Fan, C.; Husson, H. P.; De Rostolan, J.; Potier, P. 1968; 90
Bacovescu, A.; Pictet, A. 1905; 38
Lounasmaa, M.; Miettinen, J.; Hanhinen, P.; Jokela, R. 1997; 38
Guibe, F.; Grierson, D. S.; Husson, H.-P. 1982; 23
Bur, S. K.; Knochel, P.; Molander, G. A. 2014
Tafel, J. 1892; 268
Magnus, P.; Giles, M.; Bonnert, R.; Johnson, G.; McQuire, L.; Deluca, M.; Merritt, A.; Kim, C. S.; Vicker, N. 1993; 115
Grierson, D. S.; Vuilhorgne, M.; Lemoine, G.; Husson, H. P. 1982; 47
Trost, B. M.; Caldwell, C. G.; Murayama, E.; Heissler, D. 1983; 48
Murahashi, S.-I.; Zhang, D. 2008; 37
Enders, D.; Ward, D.; Adam, J.; Raabe, G. 1996; 35
Verkade, J. M. M.; van Hemert, L. J. C.; Quaedflieg, P. J. L. M.; Rutjes, F. P. J. T. 2008; 37
Carreira, E. M.; Du Bois, J. 1995; 117
Teijaro, C. N.; Zhao, S.; Kokkonda, P.; Andrade, R. B. 2015; 47
Kutney, J. P.; Fuller, G. B. 1975; 3
Spiegel, D. A.; Wiberg, K. B.; Schacherer, L. N.; Medeiros, M. R.; Wood, J. L. 2005; 127
Sirasani, G.; Andrade, R. B. 2011; 13
Zhao, S.; Sirasani, G.; Vaddypally, S.; Zdilla, M. J.; Andrade, R. B. 2013; 52
Juillard, J. 1977; 49
Sirasani, G.; Andrade, R. B.; Michael, H. 2013; 9
Smith, G. F.; Manske, R. H. F. 1965; 8
Tedesco, R.; Fiaschi, R.; Napolitano, E. 1995; 60
Koskinen, A.; Lounasmaa, M. 1983
Savoca, A. C.; Urgaonkar, S. 2001
Head, D. L.; McCarty, C. G. 1973; 14
Kobayashi, S.; Mori, Y.; Fossey, J. S.; Salter, M. M. 2011; 111
Eisch, J. J.; Galle, J. E. 1979; 44
Hartwig, W. 1983; 39
Zhao, S.; Andrade, R. B. 2017; 82
Seybold, P. G. 2012; 64
Tafel, J. 1891; 264
Tabuchi, T.; Inanaga, J.; Yamaguchi, M. 1986; 27
Bonjoch, J.; Casamitjana, N.; Bosch, J. 1988; 44
Wenkert, E.; Chauncy, B.; Wentland, S. H. 1973; 3
Newman, D. J.; Cragg, G. M. 2007; 70
Sirasani, G.; Paul, T.; Dougherty, W.; Kassel, S.; Andrade, R. B. 2010; 75
Lamotte, J.; Dupont, L.; Dideberg, O.; Kambu, K.; Angenot, L. 1979; 20
Murahashi, S.-I. 1995; 34
Arend, M.; Westermann, B.; Risch, N. 1998; 37
Wieland, H.; Jennen, R. G. 1940; 545
Oare, D. A.; Henderson, M. A.; Sanner, M. A.; Heathcock, C. H. 1990; 55
Agami, C.; Couty, F.; Evano, G. 2000; 2
Kende, A. S.; Liu, K.; Jos Brands, K. M. 1995; 117
Grierson, D. S.; Harris, M.; Husson, H.-P. 1983; 39
Kokkonda, P.; Brown, K. R.; Seguin, T. J.; Wheeler, S. E.; Vaddypally, S.; Zdilla, M. J.; Andrade, R. B. 2015; 54
Trapencieris, P.; Pigza, J. A. 2001
Llacet, C.; Couturier, J. 1962
Zhao, S.; Sirasani, G.; Vaddypally, S.; Zdilla, M. J.; Andrade, R. B. 2016; 72
Passarella, D.; Martinelli, M.; Llor, N.; Amat, M.; Bosch, J. 1999; 55
References_xml – volume: 264
  start-page: 33
  year: 1891
  end-page: 33
  publication-title: Justus Liebigs Ann. Chem
  contributor:
    fullname: Tafel, J.
– volume: 90
  start-page: 5622
  year: 1968
  end-page: 5622
  publication-title: J. Am. Chem. Soc.
  contributor:
    fullname: Ahond, A.; Cave, A.; Kan-Fan, C.; Husson, H. P.; De Rostolan, J.; Potier, P.
– volume: 38
  start-page: 2787
  year: 1905
  end-page: 2787
  publication-title: Ber. Dtsch. Chem. Ges.
  contributor:
    fullname: Bacovescu, A.; Pictet, A.
– volume: 55
  start-page: 132
  year: 1990
  end-page: 132
  publication-title: J. Org. Chem.
  contributor:
    fullname: Oare, D. A.; Henderson, M. A.; Sanner, M. A.; Heathcock, C. H.
– volume: 111
  start-page: 2626
  year: 2011
  end-page: 2626
  publication-title: Chem. Rev.
  contributor:
    fullname: Kobayashi, S.; Mori, Y.; Fossey, J. S.; Salter, M. M.
– volume: 83
  start-page: 735
  year: 1985
  end-page: 735
  publication-title: J. Chem. Phys.
  contributor:
    fullname: Reed, A. E.; Weinstock, R. B.; Weinhold, F.
– volume: 44
  start-page: 3279
  year: 1979
  end-page: 3279
  publication-title: J. Org. Chem.
  contributor:
    fullname: Eisch, J. J.; Galle, J. E.
– volume: 117
  start-page: 10597
  year: 1995
  end-page: 10597
  publication-title: J. Am. Chem. Soc.
  contributor:
    fullname: Kende, A. S.; Liu, K.; Jos Brands, K. M.
– volume: 1996
  start-page: 1
  year: 1996
  end-page: 1
  publication-title: Synthesis
  contributor:
    fullname: Tsuji, J.; Mandai, T.
– volume: 114
  start-page: 9434
  year: 1992
  end-page: 9434
  publication-title: J. Am. Chem. Soc.
  contributor:
    fullname: Evans, D. A.; Gage, J. R.; Leighton, J. L.
– volume: 28
  start-page: 5977
  year: 1987
  end-page: 5977
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Jung, M. E.; Usui, Y.; Vu, C. T.
– volume: 70
  start-page: 461
  year: 2007
  end-page: 461
  publication-title: J. Nat. Prod.
  contributor:
    fullname: Newman, D. J.; Cragg, G. M.
– volume: 112
  start-page: 7416
  year: 1990
  end-page: 7416
  publication-title: J. Am. Chem. Soc.
  contributor:
    fullname: Nicolaou, K. C.; Hwang, C. K.; Smith, A. L.; Wendeborn, S. V.
– volume: 9
  start-page: 6217
  year: 1968
  end-page: 6217
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Sandberg, F.; Roos, K.; Ryrberg, K. J.; Kristiansson, K.
– volume: 19
  start-page: 450
  year: 1984
  end-page: 450
  publication-title: Theor. Exp. Chem.
  contributor:
    fullname: Litinskii, A. O.; Gokhberg, P. Y.; Shatkovskaya, D. B.; Bolotin, A. B.; Litinskaya, N. N.; Popov, G. P.
– volume: 38
  start-page: 1455
  year: 1997
  end-page: 1455
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Lounasmaa, M.; Miettinen, J.; Hanhinen, P.; Jokela, R.
– volume: 22
  start-page: 11593
  year: 2016
  end-page: 11593
  publication-title: Chem. - Eur. J.
  contributor:
    fullname: Zhao, S.; Teijaro, C. N.; Chen, H.; Sirasani, G.; Vaddypally, S.; Zdilla, M. J.; Dobereiner, G. E.; Andrade, R. B.
– volume: 55
  start-page: 14995
  year: 1999
  end-page: 14995
  publication-title: Tetrahedron
  contributor:
    fullname: Passarella, D.; Martinelli, M.; Llor, N.; Amat, M.; Bosch, J.
– volume: 49
  start-page: 885
  year: 1977
  end-page: 885
  publication-title: Pure Appl. Chem.
  contributor:
    fullname: Juillard, J.
– year: 2001
  publication-title: Encyclopedia of Reagents for Organic Synthesis
  contributor:
    fullname: Savoca, A. C.; Urgaonkar, S.
– volume: 47
  start-page: 1547
  year: 2015
  end-page: 1547
  publication-title: Synthesis
  contributor:
    fullname: Teijaro, C. N.; Zhao, S.; Kokkonda, P.; Andrade, R. B.
– volume: 23
  start-page: 3595
  year: 1982
  end-page: 3595
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Suzuki, M.; Yanagisawa, A.; Noyori, R.
– volume: 57
  start-page: 10383
  year: 2014
  end-page: 10383
  publication-title: J. Med. Chem.
  contributor:
    fullname: Teijaro, C. N.; Munagala, S.; Zhao, S.; Sirasani, G.; Kokkonda, P.; Malofeeva, E. V.; Hopper-Borge, E.; Andrade, R. B.
– volume: 65
  start-page: 1381
  year: 2002
  end-page: 1381
  publication-title: J. Nat. Prod.
  contributor:
    fullname: Frédérich, M.; Jacquier, M. J.; Thepenier, P.; De Mol, P.; Tits, M.; Philippe, G.; Delaude, C.; Angenot, L.; Zeches-Hanrot, M.
– volume: 125
  start-page: 4541
  year: 2003
  end-page: 4541
  publication-title: J. Am. Chem. Soc.
  contributor:
    fullname: Deiters, A.; Chen, K.; Eary, C. T.; Martin, S. F.
– volume: 2
  start-page: 1108
  year: 2012
  end-page: 1108
  publication-title: ACS Catal
  contributor:
    fullname: Schümperli, M. T.; Hammond, C.; Hermans, I.
– volume: 11
  start-page: 2085
  year: 2009
  end-page: 2085
  publication-title: Org. Lett.
  contributor:
    fullname: Sirasani, G.; Andrade, R. B.
– start-page: 821
  year: 1983
  end-page: 821
  publication-title: J. Chem. Soc., Chem. Commun.
  contributor:
    fullname: Koskinen, A.; Lounasmaa, M.
– volume: 60
  start-page: 5316
  year: 1995
  end-page: 5316
  publication-title: J. Org. Chem.
  contributor:
    fullname: Tedesco, R.; Fiaschi, R.; Napolitano, E.
– volume: 44
  start-page: 1735
  year: 1988
  end-page: 1735
  publication-title: Tetrahedron
  contributor:
    fullname: Bonjoch, J.; Casamitjana, N.; Bosch, J.
– volume: 66
  start-page: 262
  year: 2000
  end-page: 262
  publication-title: Planta Med.
  contributor:
    fullname: Frédérich, M.; De Pauw, M.-C.; Llabrès, G.; Tits, M.; Hayette, M.-P.; Brandt, V.; Penelle, J.; De Mol, P.; Angenot, L.
– volume: 39
  start-page: 513
  year: 2003
  end-page: 513
  publication-title: Chem. Nat. Compd.
  contributor:
    fullname: Frederich, M.; Tits, M.; Angenot, L.
– volume: 54
  start-page: 12632
  year: 2015
  end-page: 12632
  publication-title: Angew. Chem., Int. Ed.
  contributor:
    fullname: Kokkonda, P.; Brown, K. R.; Seguin, T. J.; Wheeler, S. E.; Vaddypally, S.; Zdilla, M. J.; Andrade, R. B.
– volume: 13
  start-page: 4736
  year: 2011
  end-page: 4736
  publication-title: Org. Lett.
  contributor:
    fullname: Sirasani, G.; Andrade, R. B.
– volume: 37
  start-page: 161
  year: 1979
  end-page: 161
  publication-title: Planta Med.
  contributor:
    fullname: Kambu, K.; Coune, C.; Angenot, L.
– volume: 41
  start-page: 1190
  year: 1727
  end-page: 1190
  publication-title: Bull. Soc. Chim. Fr
  contributor:
    fullname: Polonovski, M.; Polonovski, M.
– volume: 39
  start-page: 2609
  year: 1983
  end-page: 2609
  publication-title: Tetrahedron
  contributor:
    fullname: Hartwig, W.
– volume: 37
  start-page: 1044
  year: 1998
  end-page: 1044
  publication-title: Angew. Chem., Int. Ed.
  contributor:
    fullname: Arend, M.; Westermann, B.; Risch, N.
– volume: 48
  start-page: 3252
  year: 1983
  end-page: 3252
  publication-title: J. Org. Chem.
  contributor:
    fullname: Trost, B. M.; Caldwell, C. G.; Murayama, E.; Heissler, D.
– volume: 47
  start-page: 4439
  year: 1982
  end-page: 4439
  publication-title: J. Org. Chem
  contributor:
    fullname: Grierson, D. S.; Vuilhorgne, M.; Lemoine, G.; Husson, H. P.
– volume: 14
  start-page: 1405
  year: 1973
  end-page: 1405
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Head, D. L.; McCarty, C. G.
– year: 2001
  publication-title: Encyclopedia of Reagents for Organic Synthesis
  contributor:
    fullname: Trapencieris, P.; Pigza, J. A.
– volume: 68
  start-page: 591
  year: 2002
  end-page: 591
  publication-title: Planta Med.
  contributor:
    fullname: Lansiaux, A.; Bailly, C.; Houssier, C.; Colson, P.; De Pauw-Gillet, M. C.; Frédérich, M.; Tits, M.; Angenot, L.
– volume: 545
  start-page: 99
  year: 1940
  end-page: 99
  publication-title: Justus Liebigs Ann. Chem
  contributor:
    fullname: Wieland, H.; Jennen, R. G.
– volume: 367
  start-page: 260
  year: 2003
  end-page: 260
  publication-title: Naunyn-Schmiedeberg's Arch. Pharmacol
  contributor:
    fullname: Frederich, M.; Bentires-Ali, M.; Tits, M.; Angenot, L.; Heinen, E.; De Pauw-Gillet, M. C.
– volume: 53
  start-page: 6523
  year: 2012
  end-page: 6523
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Kogure, N.; Suzuki, Y.; Wu, Y.; Kitajima, M.; Zhang, R.; Takayama, H.
– volume: 20
  start-page: 4227
  year: 1979
  end-page: 4227
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Lamotte, J.; Dupont, L.; Dideberg, O.; Kambu, K.; Angenot, L.
– volume: 128
  start-page: 7164
  year: 2006
  end-page: 7164
  publication-title: J. Am. Chem. Soc.
  contributor:
    fullname: Oisaki, K.; Zhao, D.; Kanai, M.; Shibasaki, M.
– volume: 60
  start-page: 9983
  year: 2004
  end-page: 9983
  publication-title: Tetrahedron
  contributor:
    fullname: Fernandes, L.; Bortoluzzi, A. J.; Sá, M. M.
– volume: 64
  start-page: 12
  year: 2001
  end-page: 12
  publication-title: J. Nat. Prod.
  contributor:
    fullname: Frédérich, M.; De Pauw, M.-C.; Prosperi, C.; Tits, M.; Brandt, V.; Penelle, J.; Hayette, M.-P.; De Mol, P.; Angenot, L.
– volume: 19
  start-page: 2383
  year: 1978
  end-page: 2383
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Lau, P. W. K.; Chan, T. H.
– volume: 82
  start-page: 521
  year: 2017
  end-page: 521
  publication-title: J. Org. Chem.
  contributor:
    fullname: Zhao, S.; Andrade, R. B.
– volume: 23
  start-page: 5055
  year: 1982
  end-page: 5055
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Guibe, F.; Grierson, D. S.; Husson, H.-P.
– volume: 13
  start-page: 2682
  year: 2011
  end-page: 2682
  publication-title: Org. Lett.
  contributor:
    fullname: Kim, H. J.; Su, L.; Jung, H.; Koo, S.
– volume: 61
  start-page: 7873
  year: 1996
  end-page: 7873
  publication-title: J. Org. Chem.
  contributor:
    fullname: Kuehne, M. E.; Wang, T.; Seraphin, D.
– start-page: 2097
  year: 1962
  end-page: 2097
  publication-title: Bull. Soc. Chim. Fr.
  contributor:
    fullname: Llacet, C.; Couturier, J.
– volume: 37
  start-page: 1490
  year: 2008
  end-page: 1490
  publication-title: Chem. Soc. Rev.
  contributor:
    fullname: Murahashi, S.-I.; Zhang, D.
– volume: 34
  start-page: 2443
  year: 1995
  end-page: 2443
  publication-title: Angew. Chem., Int. Ed.
  contributor:
    fullname: Murahashi, S.-I.
– volume: 76
  start-page: 172
  year: 1943
  end-page: 172
  publication-title: Ber. Dtsch. Chem. Ges.
  contributor:
    fullname: Oesterlin, M.; Imoudsky, G.
– volume: 3
  start-page: 73
  year: 1973
  end-page: 73
  publication-title: Synth. Commun.
  contributor:
    fullname: Wenkert, E.; Chauncy, B.; Wentland, S. H.
– volume: 35
  start-page: 981
  year: 1996
  end-page: 981
  publication-title: Angew. Chem., Int. Ed.
  contributor:
    fullname: Enders, D.; Ward, D.; Adam, J.; Raabe, G.
– volume: 127
  start-page: 12513
  year: 2005
  end-page: 12513
  publication-title: J. Am. Chem. Soc.
  contributor:
    fullname: Spiegel, D. A.; Wiberg, K. B.; Schacherer, L. N.; Medeiros, M. R.; Wood, J. L.
– volume: 27
  start-page: 601
  year: 1986
  end-page: 601
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Tabuchi, T.; Inanaga, J.; Yamaguchi, M.
– volume: 135
  start-page: 13334
  year: 2013
  end-page: 13334
  publication-title: J. Am. Chem. Soc.
  contributor:
    fullname: Zhao, S.; Andrade, R. B.
– volume: 23
  start-page: 241
  year: 1982
  end-page: 241
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Keinan, E.; Greenspoon, N.
– volume: 77
  start-page: 400
  year: 2012
  end-page: 400
  publication-title: J. Org. Chem.
  contributor:
    fullname: McLeod, M. C.; Wilson, Z. E.; Brimble, M. A.
– volume: 75
  start-page: 3529
  year: 2010
  end-page: 3529
  publication-title: J. Org. Chem
  contributor:
    fullname: Sirasani, G.; Paul, T.; Dougherty, W.; Kassel, S.; Andrade, R. B.
– volume: 84
  start-page: 16
  year: 1951
  end-page: 16
  publication-title: Chem. Ber.
  contributor:
    fullname: Boit, H.-G.
– volume: 115
  start-page: 8116
  year: 1993
  end-page: 8116
  publication-title: J. Am. Chem. Soc.
  contributor:
    fullname: Magnus, P.; Giles, M.; Bonnert, R.; Johnson, G.; McQuire, L.; Deluca, M.; Merritt, A.; Kim, C. S.; Vicker, N.
– volume: 301
  start-page: 285
  year: 1898
  end-page: 285
  publication-title: Justus Liebigs Ann. Chem
  contributor:
    fullname: Tafel, J.
– volume: 8
  start-page: 591
  year: 1965
  end-page: 591
  publication-title: The Alkaloids: Chemistry and Physiology
  contributor:
    fullname: Smith, G. F.; Manske, R. H. F.
– volume: 268
  start-page: 229
  year: 1892
  end-page: 229
  publication-title: Justus Liebigs Ann. Chem
  contributor:
    fullname: Tafel, J.
– volume: 52
  start-page: 8309
  year: 2013
  end-page: 8309
  publication-title: Angew. Chem., Int. Ed.
  contributor:
    fullname: Zhao, S.; Sirasani, G.; Vaddypally, S.; Zdilla, M. J.; Andrade, R. B.
– volume: 39
  start-page: 3683
  year: 1983
  end-page: 3683
  publication-title: Tetrahedron
  contributor:
    fullname: Grierson, D. S.; Harris, M.; Husson, H.-P.
– volume: 113
  start-page: 2887
  year: 2013
  end-page: 2887
  publication-title: Chem. Rev.
  contributor:
    fullname: Noble, A.; Anderson, J. C.
– volume: 55
  start-page: 3171
  year: 1922
  end-page: 3171
  publication-title: Ber. Dtsch. Chem. Ges.
  contributor:
    fullname: Leuchs, H.; Nitschke, R.
– volume: 104
  start-page: 5753
  year: 1982
  end-page: 5753
  publication-title: J. Am. Chem. Soc.
  contributor:
    fullname: Shono, T.; Matsumura, Y.; Inoue, K.; Ohmizu, H.; Kashimura, S.
– volume: 105
  start-page: 5373
  year: 1983
  end-page: 5373
  publication-title: J. Am. Chem. Soc.
  contributor:
    fullname: Overman, L. E.; Lesuisse, D.; Hashimoto, M.
– volume: 117
  start-page: 8106
  year: 1995
  end-page: 8106
  publication-title: J. Am. Chem. Soc.
  contributor:
    fullname: Carreira, E. M.; Du Bois, J.
– volume: 50
  start-page: 3019
  year: 1985
  end-page: 3019
  publication-title: J. Org. Chem.
  contributor:
    fullname: Heathcock, C. H.; Henderson, M. A.; Oare, D. A.; Sanner, M. A.
– volume: 72
  start-page: 6107
  year: 2016
  end-page: 6107
  publication-title: Tetrahedron
  contributor:
    fullname: Zhao, S.; Sirasani, G.; Vaddypally, S.; Zdilla, M. J.; Andrade, R. B.
– volume: 2
  start-page: 2085
  year: 2000
  end-page: 2085
  publication-title: Org. Lett.
  contributor:
    fullname: Agami, C.; Couty, F.; Evano, G.
– volume: 9
  start-page: 1
  year: 2013
  end-page: 1
  publication-title: Strategies and Tactics in Organic Synthesis
  contributor:
    fullname: Sirasani, G.; Andrade, R. B.; Michael, H.
– volume: 43
  start-page: 2923
  year: 1978
  end-page: 2923
  publication-title: J. Org. Chem.
  contributor:
    fullname: Still, W. C.; Kahn, M.; Mitra, A.
– volume: 8
  start-page: 2973
  year: 2006
  end-page: 2973
  publication-title: Org. Lett.
  contributor:
    fullname: Utsugi, M.; Miyano, M.; Nakada, M.
– volume: 64
  year: 2012
  publication-title: Adv. Quantum Chem.
  contributor:
    fullname: Seybold, P. G.
– volume: 31
  start-page: 2689
  year: 1966
  end-page: 2689
  publication-title: J. Org. Chem.
  contributor:
    fullname: Wenkert, E.; Sklar, R.
– volume: 37
  start-page: 29
  year: 2008
  end-page: 29
  publication-title: Chem. Soc. Rev.
  contributor:
    fullname: Verkade, J. M. M.; van Hemert, L. J. C.; Quaedflieg, P. J. L. M.; Rutjes, F. P. J. T.
– volume: 3
  start-page: 197
  year: 1975
  end-page: 197
  publication-title: Heterocycles
  contributor:
    fullname: Kutney, J. P.; Fuller, G. B.
– start-page: 755
  year: 2014
  end-page: 755
  publication-title: Comprehensive Organic Synthesis II
  contributor:
    fullname: Bur, S. K.; Knochel, P.; Molander, G. A.
– volume: 102
  start-page: 1064
  year: 1980
  end-page: 1064
  publication-title: J. Am. Chem. Soc.
  contributor:
    fullname: Grierson, D. S.; Harris, M.; Husson, H. P.
– volume: 9
  start-page: 4931
  year: 2007
  end-page: 4931
  publication-title: Org. Lett.
  contributor:
    fullname: Nishimoto, Y.; Yasuda, M.; Baba, A.
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Snippet It was developed a concise synthetic route resulting in the first syntheses of bis-Strychnos alkaloids (-)-sungucine, (-)-isosungucine, and (-)-strychnogucine...
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SubjectTerms CHEMISTRY, MULTIDISCIPLINARY
Title Synthesis of Bis-Strychnos Alkaloids (–)-Sungucine, (–)-Isosungucine, and (–)-Strychnogucine B from (–)-Strychnine
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Volume 30
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