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 2013; 45(7): 959-965
DOI: 10.1055/s-0032-1316865
DOI: 10.1055/s-0032-1316865
paper
Asymmetric Synthesis of Synargentolide A and Its 3-Epimer Using the RAMP-Hydrazone Methodology
Further Information
Publication History
Received: 14 February 2013
Accepted: 15 February 2013
Publication Date:
07 March 2013 (online)
Abstract
Synargentolide A was synthesized in 11 steps starting from the commercially available 2,2-dimethyl-1,3-dioxan-5-one, employing the SAMP/RAMP-methodology via an α,α′-bis-alkylation to generate the first two stereogenic centers with virtually complete asymmetric induction (de, ee >99%). After the asymmetric synthesis of the triol fragment of the molecule, the δ-lactone moiety was constructed using an asymmetric allylation, esterification, and ring-closing metathesis sequence.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1 Collett LA, Davies-Coleman MT, Rivett DE. A. Phytochemistry 1998; 48: 651
- 2 Marco JA, Carda M, Murga J, Falomir E. Tetrahedron 2007; 63: 2929
- 3a Hoffmann HM. R, Rabe J. Angew. Chem., Int. Ed. Engl. 1985; 24: 94
- 3b Rychnovsky SD. Chem. Rev. 1995; 95: 2021
- 3c Inayat-Hussain SH, Annuar BO, Din LB, Ali AM, Ross D. Toxicol. in Vitro 2003; 17: 433
- 3d Kikuchi H, Sasaki K, Sekiya JI, Maeda Y, Amagai A, Kubohara Y, Oshima Y. Bioorg. Med. Chem. 2004; 12: 3203
- 4 García-Fortanet J, Murga J, Carda M, Marco JA. ARKIVOC 2005; (ix): 175
- 5a Sabitha G, Gopal P, Reddy CN, Yadav JS. Tetrahedron Lett. 2009; 50: 6298
- 5b Prasad KR, Penchalaiah K. Tetrahedron: Asymmetry 2010; 21: 2853
- 5c Kamal A, Balakrishna M, Reddy PV, Faazil S. Tetrahedron: Asymmetry 2010; 21: 2517
- 5d Das B, Balasubramanyam P, Veeranjaneyulu B, Chinna Reddy G. Helv. Chim. Acta 2011; 94: 881
- 5e Sabitha G, Reddy SS. S, Raju A, Yadav JS. Synthesis 2011; 1279
- 6 Sabitha G, Fatima N, Gopal P, Reddy CN, Yadav JS. Tetrahedron: Asymmetry 2009; 20: 184
- 7a Enders D, Voith M, Lenzen A. Angew. Chem. Int. Ed. 2005; 44: 1304
- 7b Enders D, Breukers S, Reichenbach LF. 2,2-Dimethyl-1,3-dioxan-5-one. In Electronic Encyclopedia of Reagents for Organic Synthesis . Rovis T. Wiley; Chichester: 2012
- 8a Enders D, Eichenauer H. Chem. Ber. 1979; 112: 2933
- 8b Job A, Janeck CF, Bettray W, Peters R, Enders D. Tetrahedron 2002; 58: 2253
- 8c Lazny R, Nodzewska A. Chem. Rev. 2010; 110: 1386
- 9a Enders D, Voith M, Ince SJ. Synthesis 2002; 1775
- 9b Nicolaou KC, Brenzovich WE, Bulger PG, Francis TM. Org. Biomol. Chem. 2006; 4: 2119
- 10 Enders D, Hundertmark T, Lazny R. Synlett 1998; 721
- 11 Dess DB, Martin JC. J. Org. Chem. 1983; 48: 4155
- 12a Cossy J, BouzBouz S, Hoveyda AH. J. Organomet. Chem. 2001; 624: 327
- 12b BouzBouz S, Cossy J. Org. Lett. 2003; 5: 1995
- 13 Enders D, Fey P, Kipphardt H. Org. Synth. Coll. Vol. 8 . Wiley; New York: 1993