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Synthesis 2014; 46(21): 2945-2950
DOI: 10.1055/s-0034-1378565
DOI: 10.1055/s-0034-1378565
paper
Stereoselective Total Synthesis of epi-Phomopsolide B
Autor*innen
Weitere Informationen
Publikationsverlauf
Received: 08. Mai 2014
Accepted after revision: 07. Juli 2014
Publikationsdatum:
12. August 2014 (online)
Abstract
The stereoselective total synthesis of epi-phomopsolide B, a polyhydroxy lactone natural product, has been accomplished. Starting from the commercially available diethyl l-tartrate, the synthesis involved an asymmetric Evans aldol approach and Still–Gennari olefination. Further, the resulting epi-phomopsolide B was screened for cytotoxicity and antimicrobial properties, and the outcome is presented.
Key words
asymmetric Evans aldol approach - Still–Gennari olefination - diethyl l-tartrate - total synthesisSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/
10.1055/s-00000084. Included are 1H and 13C NMR spectra of representative compounds and procedures for the evaluation of biological
activity.
- Supporting Information (PDF) (opens in new window)
-
References
- 1a Hoffmann HM. R, Rabe J. Angew. Chem., Int. Ed. Engl. 1985; 24: 94
- 1b Negishi E, Kotora M. Tetrahedron 1997; 53: 6707
- 1c Collins I. J. Chem. Soc., Perkin Trans. 1 1999; 1377
- 2a Leite L, Jansone D, Veveris M, Cirule H, Popelis Y, Melikyan G, Avetisyan A, Lukevics E. Eur. J. Med. Chem. 1999; 34: 859
- 2b Hilmi F, Gertsch J, Bremner P, Valovic S, Heinrich M, Sticher O, Heilmann J. Bioorg. Med. Chem. 2003; 11: 3659
- 3a Davies-Coleman MT, Rivett DE. A. Prog. Chem. Org. Nat. Prod. 1989; 55: 1
- 3b Dickinson JM. Nat. Prod. Rep. 1993; 10: 71
- 4 Grove JF. J. Chem. Soc., Perkin Trans. 1 1985; 865
- 5 Santamour FS, Bentz SE. J. Arboricult. 1995; 21: 122
- 6 Stierle DB, Stierle AA, Ganser B. J. Nat. Prod. 1997; 60: 1207
- 7 Yuan L, Lin X, Zhao P.-J, Ma J, Huang Y.-J, Shen Y.-M. Helv. Chim. Acta 2009; 92: 1184
- 8 Reddy EN, Krishnaiah A, Rao TP. Tetrahedron: Asymmetry 2013; 24: 724
- 9a Noshita T, Sugiyama T, Yamashita K. Agric. Biol. Chem. 1991; 55: 1207
- 9b Noshita T, Sugiyama T, Yamashita K, Oritani T. Biosci., Biotechnol., Biochem. 1994; 58: 740
- 10 Prasad KR, Gutala P. Tetrahedron 2012; 68: 7489
- 11 Valverde S, Herradon B, Rabanal RM, Lomas MM. Can. J. Chem. 1987; 65: 332
- 12 Kamal A, Reddy PV, Prabhakar S. Tetrahedron: Asymmetry 2009; 20: 1936
- 13 Zhang W, Carter RG. Org. Lett. 2005; 7: 4209
- 15 Still WC, Gennari C. Tetrahedron Lett. 1983; 24: 4405
- 16 Gross U, Nieger M, Bras S. Chem. Eur. J. 2010; 16: 11624
- 17 Shimada K, Kaburagi Y, Fukuyama T. J. Am. Chem. Soc. 2003; 125: 4048