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Synlett 2013; 24(6): 757-761
DOI: 10.1055/s-0032-1318305
DOI: 10.1055/s-0032-1318305
letter
A Biomimetic Approach to Terpenes Isolated from Marine Sponges: a Ugi Coupling Reaction in a Hypothetical Biosynthesis
Further Information
Publication History
Received: 28 December 2012
Accepted after revision: 01 February 2013
Publication Date:
06 March 2013 (online)
Abstract
A unique pathway for the biosynthesis of marine sponge terpenes is proposed. Based on this proposal, a biomimetic approach using a Ugi coupling reaction has been designed and applied to the efficient construction of the right-side, peptide-like portions of boneratamides and exigurin.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References
- 1a Ichikawa Y. Chem. Lett. 1990; 1347
- 1b Ichikawa Y. Synlett 1991; 715
- 1c Ichikawa Y. J. Chem. Soc., Perkin Trans. 1 1992; 2135
- 1d Ichikawa Y, Yamazaki M, Isobe M. J. Chem. Soc., Perkin Trans. 1 1993; 2429
- 1e Ichikawa Y, Matsuda Y, Okumura K, Nakamura M, Masuda T, Kotsuki H, Nakano K. Org. Lett. 2011; 13: 2520
- 2a Williams DE, Patrick BO, Tahir A, Van Soest R, Roberge M, Andersen RJ. J. Nat. Prod. 2004; 67: 1752
- 2b Blunt JW, Copp BR, Munro MH. G, Northcote PT, Prinsep MR. Nat. Prod. Rep. 2006; 23: 26
- 3a Di Blasio B, Fattorusso E, Magno S, Mayol L, Pedone C, Santacroce C, Sica D. Tetrahedron 1976; 32: 473
- 3b Caine D, Deutsch H. J. Am. Chem. Soc. 1978; 100: 8030
- 4a Ugi I. Angew. Chem., Int. Ed. Engl. 1962; 1: 8
- 4b Ugi I. Angew. Chem., Int. Ed. Engl. 1982; 21: 810
- 4c Dömling A, Ugi I. Angew. Chem. Int. Ed. 2000; 39: 3168
- 4d Dömling A. Chem. Rev. 2006; 106: 17
- 5 Tanaka N, Suto S, Ishiyama H, Kubota T, Yamano A, Shiro M, Fromont J, Kobayashi J. Org. Lett. 2012; 14: 3498
- 6 Endo A, Yanagisawa A, Abe M, Tohma S, Kan T, Fukuyama T. J. Am. Chem. Soc. 2002; 124: 6552
- 7a Ugi I, Steinbrückner C. Chem. Ber. 1961; 94: 2802
- 7b Isenring HP, Hofheinz W. Synthesis 1981; 385
- 7c Hatanaka M, Yamamoto Y, Nitta H, Ishimaru T. Tetrahedron Lett. 1981; 22: 3883
- 7d Gedey S, Van der Eycken J, Fülöp F. Org. Lett. 2002; 4: 1967
- 8 Liu Z, Nefzi A. J. Comb. Chem. 2010; 12: 566
- 9 A solution of l-glutamic acid 1-methyl ester (13; 430 mg, 2.67 mmol) and acetone (8; 1.30 mL, 17.8 mmol) in MeOH (25.0 mL) was treated with tert-butyl isocyanide (12; 0.20 mL, 1.78 mmol). After stirring at r.t. for 1.5 h, the solution was heated at 50 °C for 24 h, followed by refluxing for 1 h. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in EtOAc and H2O. The organic layer was separated, and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried (Na2SO4) and concentrated to afford the residue, which was purified by silica gel chromatography to furnish γ-lactam 15 (337 mg, 67%).
- 10 The Ugi reaction using polymer-supported glutamic acid derivatives on the solid phase to produce N-substituted pyrrolidinones has been reported. For reference, see: Hulme C, Dietrich J. Mol. Diversity 2009; 13: 195
- 11a Demharter A, Hörl W, Herdtweck E, Ugi I. Angew. Chem., Int. Ed. Engl. 1996; 35: 173
- 11b Ugi I, Demharter A, Hörl W, Schmid T. Tetrahedron 1996; 52: 11657
- 12 See the Supporting Information
- 13 Ito M, Koyakumaru K, Ohta T, Takaya H. Synthesis 1995; 376
- 14 Uy MM, Ohta S, Yanai M, Ohta E, Hirata T, Ikegami S. Tetrahedron 2003; 59: 731
- 15 Suto S, Tanaka N, Fromont J, Kobayashi J. Tetrahedron Lett. 2011; 52: 3470