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Synthesis 2016; 48(23): 4213-4220
DOI: 10.1055/s-0035-1562778
DOI: 10.1055/s-0035-1562778
paper
Total Synthesis of the Proposed Structures of the Novel Antimalarial Pyranone Cryptorigidifoliol E
Further Information
Publication History
Received: 14 June 2016
Accepted after revision: 16 June 2016
Publication Date:
02 August 2016 (online)
Abstract
The total syntheses of the proposed structures of the antimalarial lactone cryptorigidifoliol E are described. The synthetic sequence notably features a Bartlett–Smith halocyclization to give a chiral epoxide, followed by its regioselective ring-opening reaction, Still–Gennari olefination, Corey–Bakshi–Shibata (CBS) ynone reduction, and olefin cross-metathesis.
Key words
total synthesis - cryptorigidifoliol E - lactones - Bartlett–Smith halocyclization - Corey–Bakshi–Shibata reduction - cross-metathesisSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562779.
- Supporting Information
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References
- 1a Macro JA, Carda M, Murga J, Falomir E. Tetrahedron 2007; 63: 2929 ; and references cited therein
- 1b Drewes SE, Sehlapelo BM, Horn MM, Scott-Shaw R, Sandor O. Phytochemistry 1995; 38: 1427
- 2 Liu Y, Rakotondraibe LH, Brodie PJ, Wiley JD, Cassera MB, Miller JS, Ratovoson F, Rakotobe E, Rasamison VE, Kingston D. J. Nat. Prod. 2015; 78: 1330
- 3a Radha Krishna P, Ramana Reddy VV. Tetrahedron Lett. 2005; 46: 3905
- 3b Radha Krishna P, Srinivas Reddy P. Tetrahedron 2007; 63: 3995
- 3c Radha Krishna P, Srinivas R. Tetrahedron Lett. 2007; 48: 2013
- 3d Radha Krishna P, Srinivas R. Tetrahedron: Asymmetry 2007; 18: 2197
- 3e Radha Krishna P, Srinivas P. Tetrahedron Lett. 2010; 51: 2295
- 3f Radha Krishna P, Rajesh N, Ramesh K. Synthesis 2014; 46: 307
- 3g Dayaker G, Radha Krishna P. Helv. Chim. Acta 2014; 97, 868
- 3h Manikanta G, Raju G, Radha Krishna P. RSC Adv. 2015; 5: 7964
- 4 Kumar JN, Das B. RSC Adv. 2015; 5: 14465
- 5 Bartlett PA, Meadows JD, Brown EG, Morimoto A, Jernstedt KK. J. Org. Chem. 1982; 47: 4013
- 6a Schleicher KD, Jamison TF. Beilstein J. Org. Chem. 2013; 9: 1533
- 6b Rajesh K, Suresh V, Selvam JJ. P, Rao CB, Venkateswarlu Y. Helv. Chim. Acta 2009; 92: 1866
- 7a Rychnovsky SD, Skalitzky DJ. Tetrahedron Lett. 1990; 31: 945
- 7b Evans DA, Rieger DL, Gage JR. Tetrahedron Lett. 1990; 31: 7099
- 7c Rychnovsky SD, Rogers B, Yang G. J. Org. Chem. 1993; 58: 3511
- 8 Still WC, Gennari C. Tetrahedron Lett. 1983; 24: 4405
- 9 Corey EJ, Fuchs PL. Tetrahedron Lett. 1972; 3769
- 10a Corey EJ, Bakshi RK. J. Am. Chem. Soc. 1987; 109: 5551
- 10b Radha Krishna P, Anitha K. Helv. Chim. Acta 2011; 94: 1246
- 10c Parker KA, Ledeboer MW. J. Org. Chem. 1996; 61: 3214
- 10d Pichlmair S, de Lera Ruiz M, Basu K, Paquette LA. Tetrahedron 2006; 62: 5178
- 11a Chatterjee AK, Grubbs RH. Angew. Chem. Int. Ed. 2002; 41: 3171
- 11b Trost BM, Aponick A. J. Am. Chem. Soc. 2006; 128: 3931
- 11c Grubbs RH. Tetrahedron 2004; 60: 7117
- 11d Radha Krishna P, Dayaker G. Tetrahedron Lett. 2007; 48: 7279
- 11e Radha Krishna P, Shiva Kumar E. Tetrahedron Lett. 2009; 50: 6676