RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2012; 23(10): 1485-1488
DOI: 10.1055/s-0031-1290678
DOI: 10.1055/s-0031-1290678
letter
A Concise Asymmetric Synthesis of (–)-Virolin, (–)-Surinamensin, (–)-Raphidecursinol B and (–)-Polysphorin
Weitere Informationen
Publikationsverlauf
Received: 14. März 2012
Accepted: 03. April 2012
Publikationsdatum:
29. Mai 2012 (online)
Abstract
Highly concise and general asymmetric syntheses of biologically important natural (–)-8,4′-oxyneolignans [(–)-virolin, (–)-surinamensin, (–)-raphidecursinol B, and (–)-polysphorin] are reported. The key step in the synthesis is the Evan’s syn-aldol reaction to achieve the adducts with the desired stereochemistry. The four biologically important plant metabolites were synthesized using two common intermediates.
Key words
asymmetric synthesis - chiral auxiliary - aldol reaction - natural products - oxyneolignansSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References
- 1 Moss GP. Pure Appl. Chem. 2000; 72: 1493
- 2a Barata LE. S, Baker PM, Gottlieb OR, Ruveda EA. Phytochemistry 1978; 17: 783
- 2b Barata LE. S, Santos LS, Ferri PH, Phillipson JD, Paine A, Croft SL. Phytochemistry 2000; 55: 589
- 2c Zhang HJ, Tamez PA, Hoang VD, Tan GT, Van Hung N, Xuan LT, Huong LM, Cuong NM, Thao DT, Soejarto DD, Fong HH. S, Pezzuto JM. J. Nat. Prod. 2001; 64: 772
- 2d Ma Y, Han GQ, Li CL, Arison BH, Hwang SB. Acta Pharm. Sin. 1991; 26: 345
- 3a Ridley RG. Nature (London) 2002; 415: 686
- 3b Miller LH, Baruch DI, Marsh K, Doumbo OK. Nature (London) 2002; 415: 673
- 4a Andreazza CM. C, Takahata Y. J. Mol. Struct. (THEOCHEM) 2003; 625: 257
- 4b Aveniente M, Barata LE. S, Santos EC. T, Pinto EF, Rossi BB. 24a Reuniñao Anual da SBQ 2001; Abstract Book: MD 051
- 4c Andreazza CM. C, Takahata Y. J. Mol. Struct. (THEOCHEM) 2003; 638: 21
- 5a Zacchino S, Rodríguez G, Pezzenati G, Orellana G. J. Nat. Prod. 1997; 60: 659
- 5b Zacchino S, Rodríguez G, Santocchia C, Pezzenati G, Giannini F, Enriz R. J. Ethnopharmacology 1998; 62: 35
- 5c Pinheiro AA. C, Borges RS, Santos LS, Alves CN. J. Mol. Struct. (THEOCHEM) 2004; 672: 215
- 6a Kónya K, Varga Zs, Antus S. Phytomedicine 2001; 8: 454
- 6b Ahn BT, Lee S, Lee SB, Lee ES, Kim JG, Bok SH, Jeong TS. J. Nat. Prod. 2001; 64: 1562
- 7 Alves CN, Pereira BL, Santos LS, Jardim IN. J. Braz. Chem. Soc. 1998; 9: 577
- 8a Hada S, Hattori M, Tezuka Y, Kikuchi T, Namba T. Phytochemistry 1988; 27: 563
- 8b Zacchino SA, Badano H. J. Nat. Prod. 1985; 48: 830
- 8c Zacchino S, Badano H. J. Nat. Prod. 1988; 51: 1261
- 8d Zacchino S, Badano H. J. Nat. Prod. 1991; 54: 155
- 8e Zacchino S. J. Nat. Prod. 1994; 57: 446
- 8f Li K, Helm RF. J. Chem. Soc., Perkin Trans. 1 1996; 2425
- 8g Chen X, Ren X, Peng K, Pan X, Chan AS. C, Yang TK. Tetrahedron: Asymmetry 2003; 14: 701
- 8h Sefkow M. Synthesis 2003; 2595
- 8i Shimomura H, Sashida Y, Oohara M. Phytochemistry 1987; 26: 1513
- 8j Wallis AF. A. Aust. J. Chem. 1973; 26: 585
- 8k Zanarotti A. J. Chem. Res. 1983; 306
- 9 Lee AL, Ley SV. Org. Biomol. Chem. 2003; 1: 3957
- 10 Curti C, Zanardi F, Battistini L, Sartori S, Rassu G, Pinna L, Casiraghi G. J. Org. Chem. 2006; 71: 8552
- 11 Das SK, Das SK, Panda G. Eur. J. Org. Chem. 2010; 5100
- 12 Bigot YL, Delmas M, Gaset A. Tetrahedron Lett. 1983; 24: 193
- 13 Yu J, Gaunt MJ, Spencer JB. J. Org. Chem. 2002; 67: 4627
- 14 Theodorou V, Skobridis K, Tzakos AG, Ragoussis V. Tetrahedron Lett. 2007; 48: 8230
- 15 Sreedhar B, Swapna V, Sridhar Ch. Synth. Commun. 2004; 34: 1433
- 16 Hintermann T, Seebach D. Helv. Chim. Acta 1998; 81: 2093
- 17 Evans DA, Bender SL. Tetrahedron Lett. 1986; 27: 799
- 18a Evans DA, Bartroli J, Shih TL. J. Am. Chem. Soc. 1981; 103: 2127
- 18b Davies SG, Hunter IA, Nicholson RL, Roberts PM, Savory ED, Smith AS. Tetrahedron 2004; 60: 7553
- 18c Haigh D, Birrell HC, Cantello BC. C, Eggleston DS, Haltiwanger RC, Hindley RM, Ramaswamy A, Stevens NC. Tetrahedron: Asymmetry 1999; 10: 1353
- 18d Zhang W, Carter RG, Yokochi AF. T. J. Org. Chem. 2004; 69: 2569
- 18e Kim KS, Hong SD. Tetrahedron Lett. 2000; 41: 5909
- 18f Sasaki S, Hamada Y, Shioiri T. Tetrahedron Lett. 1999; 40: 3187
- 18g Davies SG, Nicholson RL, Smith AD. Org. Biomol. Chem. 2004; 2: 3385
- 19a Stiles M, Winkler RW, Chang YL, Traynor L. J. Am. Chem. Soc. 1964; 86: 3337
- 19b House HO, Crumrine DS, Teranishi AY, Olmstead HD. J. Am. Chem. Soc. 1973; 95: 3310
- 19c Heathcock CH, Pirrung MC, Sohn JE. J. Org. Chem. 1980; 45: 1066
- 19d Heathcock CH, Buse CT, Kleschick WA, Pirrung MC, Sohn JE, Lampe J. J. Org. Chem. 1979; 44: 4294