Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 23
1,330
Views
13
CrossRef citations to date
0
Altmetric
Original Articles

Total Synthesis of (±)-Armepavines and (±)-Nuciferines From (2-Nitroethenyl)benzene Derivatives

, , , , &
Pages 3452-3466 | Received 25 Aug 2009, Published online: 05 Nov 2010

REFERENCES

  • (a) Tseng , T. H. ; Lee , Y. J. Evaluation of natural and synthetic compounds from east Asiatic folk medicinal plants on the mediation of cancer . Anti-Cancer Agents Med. Chem. 2006 , 6 , 347 – 365 , and references therein; (b) Chang , C. F. ; Yang , L. Y. ; Chang , S. W. ; Fang , Y. T. ; Lee , Y. J. Total synthesis of demethylwedelolactone and wedelolactone by Cu-mediated/Pd(0) catalysis and oxidation–cyclization . Tetrahedron 2008 , 64 , 3661 – 3666 ; (c) Cheng , C. F. ; Lai , Z. C. ; Lee , Y. J. Total synthesis of (±)-camphorataimides and (±)-himanimides by NaBH4/Ni(OAc)2 or Zn/AcOH stereoselective reduction . Tetrahedron 2008 , 64 , 4347 – 4353 .
  • (a) Zhang , A. ; Neumeyer , J. L. ; Baldessarini , R. J. Recent progress in development of dopamine receptor subtype-selective agents: Potential therapeutics for neurological and psychiatric disorders. Chem. Rev. 2007, 107, 274–302, and references therein; (b) Wright , C. W. ; Marshall , S. J. ; Russell , P. F. ; Anderson , M. M. ; Phillipson , J. D. ; Kirby , G. C. ; Warhurst , D. C. ; Schiff Jr , P. L. In vitro antiplasmodial, antiamoebic, and cytotoxic activities of some monomeric isoquinoline alkaloids. J. Nat. Prod. 2000, 63, 1638–1640; (c) Lafrance , M. ; Blaquiere , N. ; Fagnou , K. Aporphine alkaloid synthesis and diversification via direct arylation. Eur. J. Org. Chem. 2007, 811–825, and references therein; (d) Woo , S. H. ; Sun , N. J. ; Cassady , J. M. ; Snapka , R. M. Topoisomerase II inhibition by aporphine alkaloids. Biochem. Pharmacol. 1999, 57, 1141–1145.
  • (a) Kashiwada , Y. ; Aoshima , A. ; Ikeshiro , Y. ; Chen , Y. P. ; Furukawa , H. ; Itoigawa , M. ; Fujioka , T. ; Mihashi , K. ; Cosentino , L. M. ; Morris-Natschke , S. L. ; Lee , K. H. Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera, and structure–activity correlations with related alkaloids . Bioorg. Med. Chem. 2005 , 13 , 443 – 448 ; (b) Chia , Y. C. ; Chen , K. S. ; Chang , Y. L. ; Teng , C. M. ; Wu , Y. C. Antiplatelet actions of aporphinoids from Formosan plants . Bioorg. Med. Chem. Lett. 1999 , 9 , 3295 – 3300 .
  • (a) Gulland , J. M. ; Haworth , R. D. Synthetical experiments on the aporphine alkaloids, I: Synthesis of 5,6-dimethoxyaporphine . J. Chem. Soc. 1928 , 581 – 591 ; (b) Marion , L. ; Lemay , L. ; Portelance , V. The synthesis of dl-armepavine . J. Org. Chem. 1950 , 15 , 216 – 220 ; (c) Weisbach , J. A. ; Douglas , B. An improved synthesis of noraporphines . J. Org. Chem. 1962 , 27 , 3738 – 3740 ; (d) Cava , M. P. ; Dalton , D. R. An improved synthesis of dl-anonaine . J. Org. Chem. 1966 , 31 , 1281 – 1283 ; (e) Cava , M. P. ; Mitchell , M. J. ; Havlicek , S. C. ; Lindert , A. ; Spangler , R. J. Photochemical routes to aporphines: New syntheses of nuciferine and glaucine . J. Org. Chem. 1970 , 35 , 175 – 179 ; (f) Costanza , C. ; Lenz , G. R. ; Lessor , R. A. The synthesis of oxoaporphines and phenanthrenediones from 7-hydroxydehydronoraporphines . Heterocycles 1992 , 34 , 465 – 478 ; (g) Cuny , G. D. Intramolecular ortho-arylation of phenols utilized in the synthesis of the aporphine alkaloids (±)-lirinidine and (±)-nuciferine . Tetrahedron Lett. 2003 , 44 , 8149 – 8152 ; (h) Zhang , Y. N. ; Zhong , X. G. ; Zheng , Z. P. ; Hu , X. D. ; Zuo , J. P. ; Hu , L. H. Discovery and synthesis of new immunosuppressive alkaloids from the stem of Fissistigma oldhamii (Hemsl) Merr . Bioorg. Med. Chem. 2007 , 15 , 988 – 996 ; (i) Nimgirawath , S. ; Lorpitthaya , R. ; Wanbanjob , A. ; Taechowisan , T. ; Shen , Y. M. Total synthesis and the biological activities of (±)-norannuradhapurine . Molecules 2009 , 14 , 89 – 101 .
  • Cox , E. D. ; Cook , J. M. The Pictet–Spengler condensation: A new direction for an old reaction . Chem. Rev. 1995 , 95 , 1797 – 1842 , and references therein.
  • (a) Buu-Hoï , N. P. ; Long , C. T. ; Xuong , N. D. α,α-Dimethyl-β-arylethylamines and their behavior in the Bischler-Napieralski reaction . J. Org. Chem. 1958 , 23 , 42 – 45 ; (b) Jude , Z. M.A. ; Ching , C. B. ; Bu , J. ; McCluskey , A. The first Bischler-Napieralski cyclization in a room temperature ionic liquid . Tetrahedron Lett. 2002 , 43 , 5089 – 5091 .
  • (a) Noland , W. E. The Nef reaction . Chem. Rev. 1955 , 55 , 137 – 155 , and references therein; (b) Ballini , R. ; Petrini , M. Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction) . Tetrahedron 2004 , 60 , 1017 – 1047 , and references therein.
  • (a) Ott , A. C. ; Mattano , L. A. ; Coleman , G. H. Preparation of hydroxyphenylalkanoic acids by the Willgerodt reaction . J. Am. Chem. Soc. 1946 , 68 , 2633 – 2634 ; (b) Alam , M. M. ; Adapa , S. R. Bi(OTf)3-catalyzed Baeyer–Villiger oxidation of carbonyl compounds with m-CPBA . Synth. Commun. 2003 , 33 , 59 – 63 .
  • The x-ray data for 1 is deposited at Cambridge Chrystallographic Data Centre as number CCDC708759.
  • Gusakova , L. A. ; Smirnov , B. P. ; Chistyakov , I. G. Synthesis of certain liquid crystal substances . Khim. 1968 , 22B744 .
  • Cochran , T. G. ; Huitric , A. C. Nuclear magnetic resonance as a monitor in optical resolution, II: Synthesis and resolution of cis- and trans-2-(o-bromophenyl)cyclohexylamines . J. Org. Chem. 1971 , 36 , 3046 – 3048 .
  • Bhattacharjya , A. ; Mukhopadhyay , R. ; Pakrashi , S. C. Sodium borohydride reduction of nitrostyrenes by reverse addition: A simple and efficient method for the large-scale preparation of phenylnitroethanes. Synthesis 1985, 886–887.
  • Barash , M. ; Osbond , J. M. Chemical constitution and amebicidal action, III: Synthesis of an analog of emetine and two stereoisomers of de-ethylemetine . J. Chem. Soc. 1959 , 2157 – 2168 .
  • Hartman , G. D. ; Philips , B. T. ; Halczenko , W. Iminium ion–mediated cyclizations of 4-aryl-1,4-dihydropyridines: Bridging with acetals, carbonyls, and thiocarbonyls . J. Org. Chem. 1985 , 50 , 2423 – 2427 .
  • Mndzhoyan , A. L. ; Aroyan , A. A. ; Ovsepyan , T. R. Amines and derivatives, XI: The preparation of some chloroacetamides and urethans . Khim. Nauki 1961 , 14 , 157 – 163 .
  • Kubo , A. ; Saito , N. ; Kawakami , N. ; Matsuyama , Y. ; Miwa , T. A facile synthesis of 1,2,3,4-tetrahydroisoquinolines through cyclization of O,N-acetals . Synthesis 1987 , 824 – 827 .
  • Nordlander , J. E. ; Payne , M. J. ; Njoroge , F. G. ; Balk , M. A. ; Laikos , G. D. ; Vishwanath , V. M. Friedel-Crafts acylation with N-(trifluoroacetyl)-α-amino acid chlorides: Application to the preparation of β-arylalkylamines and 3-substituted 1,2,3,4-tetrahydroisoquinolines . J. Org. Chem. 1984 , 49 , 4107 – 4111 .
  • Mori , M. ; Chiba , K. ; Ban , Y. Reactions and syntheses with organometallic compounds, 7: Synthesis of benzolactams by palladium-catalyzed amidation . J. Org. Chem. 1978 , 43 , 1684 – 1687 .
  • (a) Kaim , L. E. ; Grimaud , L. ; Lee , A. ; Perroux , Y. ; Tirla , C. First carbamates conversion to amides by simple alkyl group transfer from trialkylalanes . Org. Lett. 2004 , 6 , 381 – 383 ; (b) Ito , Y. ; Ushitora , H. Trapping of carbamic acid species with (trimethylsilyl)diazomethane . Tetrahedron 2006 , 62 , 226 – 235 .
  • Toste , F. D. ; Still , I. W. J. A new route to the synthesis of the naturally occurring benzopentathiepin varacin . J. Am. Chem. Soc. 1995 , 117 , 7261 – 7262 .
  • Lu , S. T. ; Wu , Y. C. Studies on the alkaloids of Formosan lauraceous plants, XXIX: Transformation from aporphine N-oxides to 1-(N-methyl-N-hydroxylaminoethyl)phenanthrene derivatives . Heterocycles 1985 , 23 , 3085 – 3094 .
  • Solladie , G. ; Pasturel-Jacopé , Y. ; Maignan , J. A re-investigation of resveratrol synthesis by the Perkins reaction: Application to the synthesis of aryl cinnamic acids . Tetrahedron 2003 , 59 , 3315 – 3321 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.