Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2014; 46(23): 3199-3206
DOI: 10.1055/s-0034-1378659
DOI: 10.1055/s-0034-1378659
paper
Synthesis of C-10 Tabersonine Analogues by Palladium-Catalyzed Cross-Coupling Reactions
Further Information
Publication History
Received: 09 April 2014
Accepted after revision: 25 June 2014
Publication Date:
27 August 2014 (online)
Abstract
A series of C-10-substituted tabersonine analogues have been synthesized via palladium-catalyzed cross-coupling reactions. To be specific, tabersonine reacted with NIS in TFA to generate the 10-iodotabersonine, which participated in palladium-catalyzed or palladium/copper co-catalyzed cross-coupling reactions, such as Suzuki–Miyaura cross-coupling reaction, Heck reaction, and Sonogashira cross-coupling reaction, to afford C-10 tabersonine analogues. These protocols provide the possibility of introducing substituents with structural diversity and complexity into the C-10 of tabersonine for the pharmacological activity screening.
Key words
tabersonine - palladium catalysis - Suzuki–Miyaura cross-coupling reaction - Heck reaction - Sonogashira cross-coupling reactionSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
-
References
- 1a Cragg GM, Newman DJ. Biochim. Biophys. Acta 2013; 1830: 3670
- 1b Sucher NJ. Expert Opin. Drug Discov. 2013; 8: 21
- 1c Ngo LT, Okogun JI, Folk WR. Nat. Prod. Rep. 2013; 30: 584
- 1d Das B, Satyalakshmi G. Mini-Rev. Org. Chem. 2012; 9: 169
- 1e Singh SB In Chemical Biology: Approaches to Drug Discovery and Development to Targeting Disease. Civjan N. Wiley; Hoboken: 2012: 165-201
- 1f Dias DA, Urban S, Roessner U. Metabolites 2012; 2: 303
- 1g Cragg GM, Grothaus PG, Newman DJ In Plant Bioactives and Drug Discovery . Cechinel-Filho V. Wiley; Hoboken: 2012: 1-42
- 1h Opportunity, Challenge and Scope of Natural Products in Medicinal Chemistry . Mishra BB, Tiwari VK. Reseach Signpost; Trivandrum (India): 2011: 1-62
- 2a Voss ME, Ralph JM, Xie D, Manning DD, Chen X, Frank AJ, Leyhane AJ, Liu L, Stevens JM, Budde C, Surman MD, Friedrich T, Peace D, Scott IL, Wolf M, Johnson R. Bioorg. Med. Chem. Lett. 2009; 19: 1245
- 2b Bernhardt P, McCoy E, O’Connor SE. Chem. Biol. 2007; 14: 888
- 2c McCoy E, O’Connor SE. J. Am. Chem. Soc. 2006; 128: 14276
- 2d Weist S, Süssmuth RD. Appl. Microbiol. Biotechnol. 2005; 68: 141
- 2e Khosla C, Keasling JD. Nat. Rev. Drug Discov. 2003; 2: 1019
- 2f Birch AJ. Pure Appl. Chem. 1963; 7: 527
- 3a Kotha S, Lahiri K, Kashinath D. Tetrahedron 2002; 58: 9633
- 3b Suzuki A. J. Organomet. Chem. 1999; 576: 147
- 3c Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
- 4a Beletskaya IP, Cheprakov AV. Chem. Rev. 2000; 100: 3009
- 4b Dounay AB, Overman LE In The Mizoroki–Heck Reaction . Oestreich M. Wiley; Chichester: 2009. Chap. 16
- 5a Doucet H, Hierso J.-C. Angew. Chem. Int. Ed. 2007; 46: 834
- 5b Chinchilla R, Najera C. Chem. Rev. 2007; 107: 874
- 5c Chinchilla R, Najera C. Chem. Soc. Rev. 2011; 40: 5084
- 6a Handbook of Organopalladium Chemistry for Organic Synthesis . Vol. 1. Negishi E.-I. Wiley; Hoboken: 2002: 1369-1448
- 6b Mitchell TN In Metal-Catalyzed Cross-Coupling Reactions . Diederich F, Stang PJ. Wiley-VCH; Weinheim: 1998. Chap. 4
- 6c Tsuji J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century. Wiley; Hoboken: 2005
- 6d Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
- 7a Lin L, Mulholland N, Wu Q.-Y, Beattie D, Huang S.-W, Irwin D, Clough J, Gu Y.-C, Yang G.-F. J. Agric. Food Chem. 2012; 60: 4480
- 7b Runguphan W, O’Connor SE. Org. Lett. 2013; 15: 2850
- 7c Roy AD, Gruschow S, Cairns N, Goss RJ. M. J. Am. Chem. Soc. 2010; 132: 12243
- 7d Bao K, Dai Y, Zhu Z.-B, Tu F.-J, Zhang W.-G, Yao X.-S. Bioorg. Med. Chem. 2010; 18: 6708
- 7e Mc Elroy WT, De Shong P. Tetrahedron 2006; 62: 6945
- 7f Dobler MR, Bruce I, Cederbaum F, Cooke NG, Diorazio LJ, Hall RG, Irving E. Tetrahedron Lett. 2001; 42: 8281
- 7g Beaumard F, Dauban P, Dodd RH. Org. Lett. 2009; 11: 1801
- 7h Achanta S, Liautard V, Paugh R, Organ MG. Chem. Eur. J. 2010; 16: 12797
- 8a Toyota M, Ihara M. Nat. Prod. Rep. 1998; 15: 327
- 8b Saxton JE In The Alkaloids . Vol. 50. Cordell GA. Chap. 9 Academic Press; New York: 1998
- 8c Saxton JE In The Alkaloids . Vol. 51. Cordell GA. Academic Press; New York: 1998. Chap. 1
- 8d Saxton JE. Indoles, Part 4: The Monoterpenoid Indole Alkaloids. Wiley; Chichester: 1983
- 8e Herbert RB In The Monoterpenoid Indole Alkaloids, Supplement to Vol. 25, Part 4 of The Chemistry of Heterocyclic Compounds. Saxton JE. Wiley; Chichester: 1994. Chap. 1
- 8f Saxton JE In The Monoterpenoid Indole Alkaloids, Supplement to Vol. 25, Part 4 of The Chemistry of Heterocyclic Compounds. Saxton JE. Wiley; Chichester: 1994. Chap. 8
- 9a Danieli B, Lesma G, Palmisano G, Riva R. J. Chem. Soc., Perkin Trans. 1 1987; 155
- 9b Danieli B, Lesma G, Palmisano G, Riva R. J. Chem. Soc., Chem. Commun. 1984; 909
- 10a Mangeney P, Zo Andriamialisoa R, Langlois N, Langlois Y, Potier P. J. Am. Chem. Soc. 1979; 101: 2243
- 10b Langlois N, Gueritte G, Langlois Y, Potier P. J. Am. Chem. Soc. 1976; 98: 7017
- 10c Potier P, Langlois N, Langlois Y, Gueritte F. J. Chem. Soc., Chem. Commun. 1975; 670
- 10d Kutney JP, Ratcliffe AH, Treasurywala AM, Wunderly S. Heterocycles 1975; 3: 639
- 11a Rahman A.-U, Basha A. Biosynthesis of Indole Alkaloids . Clarendon Press; Oxford: 1983
- 11b Scott AI. Acc. Chem. Res. 1970; 3: 151
- 12 Luo X, Cai X, Liu Y, Li Y, Xia C, Shi H. Chinese Patent CN102558178, 2012 ; Chem. Abstr. 2012, 157, 229874.
- 13 Racz-Kotilla E. Herba Hungarica 1975; 14: 57
- 14 Lewin G, Rolland Y, Poisson J. Heterocycles 1980; 14: 1915
- 15 Johnson PD, Sohn J.-H, Rawal VH. J. Org. Chem. 2006; 71: 7899
- 16 Zhang D, Sun H, Zhang L, Zhou Y, Li C, Jiang H, Chen K, Liu H. Chem. Commun. 2012; 48: 2909
- 17 Ueda T, Konishi H, Manabe K. Org. Lett. 2012; 14: 3100