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Synlett 2015; 26(13): 1852-1856
DOI: 10.1055/s-0034-1380422
DOI: 10.1055/s-0034-1380422
letter
Synthesis of the C6–C14 Fragment of Euphosalicin
Weitere Informationen
Publikationsverlauf
Received: 09. April 2015
Accepted after revision: 07. Mai 2015
Publikationsdatum:
19. Juni 2015 (online)
Abstract
The synthesis of the C6–C14 fragment of euphosalicin, a highly oxygenated modified jatrophane diterpene, is described. Key steps in the preparation of this versatile intermediate are an Ireland–Claisen rearrangement and a Shibasaki direct asymmetric aldol reaction.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380422.
- Supporting Information
-
References and Notes
- 1 Current address: Uwe Rinner, Institute of Organic Chemistry, Johannes Kepler University Linz, Altenberger Straße 69, 4040 Linz, Austria.
- 2a Mwine JT, Van Damme P. J. Med. Plants Res. 2011; 5: 652
- 2b Graham JG, Quinn ML, Fabricant DS, Farnsworth NR. J. Ethnopharmacol. 2000; 73: 347
- 3a Shi QW, Su XH, Kiyota H. Chem. Rev. 2008; 108: 4295
- 3b Vasas A, Hohmann J. Chem. Rev. 2014; 114: 8579
- 4a Rinner U. Eur. J. Org. Chem. 2015; 15: 3197
- 4b Smith AB, Guaciaro MA, Schow SR, Wovkulich PM, Toder BH, Hall TW. J. Am. Chem. Soc. 1981; 103: 219
- 4c Smith AB, Lupo AT, Ohba M, Chen K. J. Am. Chem. Soc. 1989; 111: 6648
- 4d Gyorkos AC, Stille JK, Hegedus LS. J. Am. Chem. Soc. 1990; 112: 8465
- 4e Han Q, Wiemer DF. J. Am. Chem. Soc. 1992; 114: 7692
- 4f Helmboldt H, Rehbein J, Hiersemann M. Tetrahedron Lett. 2004; 45: 289
- 4g Helmboldt H, Köhler D, Hiersemann M. Org. Lett. 2006; 8: 1573
- 4h Helmboldt H, Hiersemann M. J. Org. Chem. 2009; 74: 1698
- 4i Schnabel C, Hiersemann M. Org. Lett. 2009; 11: 2555
- 4j Yamamura S, Shizuri Y, Kosemura S, Ohtsuka J, Tayama T, Ohba S, Ito M, Saito Y, Terada Y. Phytochemistry 1989; 28: 3421
- 4k Gilbert M, Galkina A, Mulzer J. Synlett 2004; 2558
- 4l Mulzer J, Giester G, Gilbert M. Helv. Chim. Acta 2005; 88: 1560
- 4m Shimokawa K, Takamura H, Uemura D. Tetrahedron Lett. 2007; 48: 5623
- 4n Lentsch C, Rinner U. Org. Lett. 2009; 11: 5326
- 4o Mohan P, Koushik K, Fuertes MJ. Tetrahedron Lett. 2012; 53: 2730
- 4p Mohan P, Fuertes MJ. Tetrahedron Lett. 2013; 54: 3919
- 4q Fürst R, Rinner U. J. Org. Chem. 2013; 78: 8748
- 4r Fürst R, Lentsch C, Rinner U. Eur. J. Org. Chem. 2013; 2293
- 4s Lentsch C, Fürst R, Rinner U. Synlett 2013; 24: 2665
- 4t Lentsch C, Fürst R, Mulzer J, Rinner U. Eur. J. Org. Chem. 2014; 919
- 4u Fürst R, Lentsch C, Rinner U. Synthesis 2014; 46: 357
- 5 Hohmann J, Evanics F, Dombi G, Molnar J, Szabo P. Tetrahedron 2001; 57: 211
- 6 Vasas A, Sulyok E, Redei D, Forgo P, Szabo P, Zupko I, Berenyi A, Molnar J, Hohmann J. J. Nat. Prod. 2011; 74: 1453
- 7 Goldman B. J. Nat. Cancer Inst. 2003; 95: 255
- 8 Eckford PD. W, Sharom FJ. Chem. Rev. 2009; 109: 2989
- 9 For a general overview, see: The Claisen Rearrangement: Methods and Applications. Hiersemann M, Nubbemeyer U. Wiley-VCH; Weinheim: 2007
- 10 Evans DA, Bartroli J, Shih TL. J. Am. Chem. Soc. 1981; 103: 2127
- 11 Neises B, Steglich W. Angew. Chem., Int. Ed. Engl. 1978; 17: 522
- 12 Evans DA, Rajapakse HA, Chiu A, Stenkamp D. Angew. Chem. Int. Ed. 2002; 41: 4573
- 13 Kallmerten J, Gould TJ. Tetrahedron Lett. 1983; 24: 5177
- 14 Picoul W, Urchegui R, Haudrechy A, Langlois Y. Tetrahedron Lett. 1999; 40: 4797
- 15 Chromatographic separation proved to be impossible. The ratio of stereoisomers was solely determined based on NMR data.
- 16 Nicolaou KC, Harrison ST. J. Am. Chem. Soc. 2007; 129: 429
- 17 Hirao T, Hayashi K, Fujihara Y, Ohshiro Y, Agawa T. J. Org. Chem. 1985; 50: 279
- 18a Brown HC, Desai MC, Jadhav PK. J. Org. Chem. 1982; 47: 5065
- 18b Sun H, Roush WR. Org. Synth. 2011; 88: 87
- 19 Duthaler RO, Hafner A. Chem. Rev. 1992; 92: 807
- 20 Tsuji J, Nagashima H, Nemoto H. Org. Synth. 1984; 62: 9
- 21 Fujii K, Maki K, Kanai M, Shibasaki M. Org. Lett. 2003; 5: 733
- 22 See the Supporting Information for a detailed description of our setup.
- 23 Matsumura K, Hashiguchi S, Ikariya T, Noyori R. J. Am. Chem. Soc. 1997; 119: 8738
- 24 The relative stereochemistry was proven via NOE correlation analysis of a cyclic acetonide analogue of 23.
- 25 Ohkubo M, Hirai G, Sodeoka M. Angew. Chem. Int. Ed. 2009; 48: 3862
- 26 Trost BM, Ball ZT. J. Am. Chem. Soc. 2001; 123: 12726
- 27 Gao F, Hoveyda AH. J. Am. Chem. Soc. 2010; 132: 10961
- 28 Zhang HX, Guibe F, Balavoine G. J. Org. Chem. 1990; 55: 1857