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Synthesis 2014; 46(06): 817-821
DOI: 10.1055/s-0033-1338584
DOI: 10.1055/s-0033-1338584
paper
Asymmetric Formal Synthesis of (+)-Pyrenolide D
Further Information
Publication History
Received: 13 November 2013
Accepted after revision: 19 December 2013
Publication Date:
23 January 2014 (online)
Abstract
A concise, asymmetric formal synthesis of (+)-pyrenolide D from (E)-crotonaldehyde is described. The key steps include an enantioselective Sharpless dihydroxylation of protected hex-4-en-1-yn-3-ol and a highly diastereoselective palladium-catalysed oxycarbonylation of (2R,3S,4S)-hex-5-ene-2,3,4-triol using iron pentacarbonyl as the carbon monoxide source.
Key words
natural products - pyrenolide D - oxycarbonylation - palladium catalysis - iron pentacarbonylSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1 Nukina M, Hirota H. Biosci., Biotechnol., Biochem. 1992; 56: 1158
- 2 Nukina M, Iikeda M, Sassa T. Agric. Biol. Chem. 1980; 44: 2761
- 3 Ackland MJ, Hanson JR, Hitchcock PB, Ratcliffe AH. J. Chem. Soc., Perkin Trans. 1 1985; 843
- 4 Engstrom KM, Mendoza MR, Navarro-Villalobos M, Gin DY. Angew. Chem. Int. Ed. 2001; 40: 1128
- 5 Thirupathi B, Reddy PP, Mohapatra DK. J. Org. Chem. 2011; 76: 9835
- 6 Zhang Ch, Liu J, Du Y. Tetrahedron Lett. 2013; 54: 3278
- 7a Pavlakos E, Georgiou T, Tofi M, Montagnon T, Vassilikogiannakis G. Org. Lett. 2009; 11: 4556
- 7b Montagnon T, Tofi M, Vassilikogiannakis G. Acc. Chem. Res. 2008; 41: 1001
- 8a Gracza T, Jäger V. Synlett 1992; 191
- 8b Gracza T, Jäger V. Synthesis 1994; 1359
- 8c Babjak M, Kapitán P, Gracza T. Tetrahedron Lett. 2002; 43: 6983
- 8d Babjak M, Kapitán P, Gracza T. Tetrahedron 2005; 61: 2471
- 8e Dixon DJ, Ley SV, Gracza T, Szolcsányi P. J. Chem. Soc., Perkin Trans. 1 1999; 839
- 8f Palík M, Karlubíková O, Lásiková A, Kožíšek J, Gracza T. Eur. J. Org. Chem. 2009; 709
- 8g Karlubíková O, Palík M, Lásiková A, Gracza T. Synthesis 2010; 3449
- 8h Szolcsányi P, Gracza T, Špánik I. Tetrahedron Lett. 2008; 49: 1357
- 8i Karlubíková O, Babjak M, Gracza T. Tetrahedron 2011; 67: 4980
- 9a Gracza T, Hasenohrl T, Stahl U, Jäger V. Synthesis 1991; 1108
- 9b Gracza T In Stereoselective Synthesis of Drugs & Natural Products . Vol. 1. Andrushko V, Andrushko N. Wiley; Hoboken: 2013: 421-440
- 9c Babjak M, Remeň Ľ, Szolcsányi P, Zálupský P, Miklóš D, Gracza T. J. Organomet. Chem. 2006; 691: 928
- 10 Spino C, Thibault C, Gingras S. J. Org. Chem. 1998; 63: 5283
-
11 Kolb HC, Van Nieuwenhze MS, Sharpless KB. Chem. Rev. 1994; 94: 2483
- 12 Yoshida K, Imamoto T. J. Am. Chem. Soc. 2005; 127: 10470
- 13 The enantioselectivity of the AD reaction was identified retrospectively based on the ee values of lactones d-ido-10 and d-galacto-10.
- 14 Rawat V, Dey S, Sudalai A. Org. Biomol. Chem. 2012; 10: 3988
- 15 Babjak M, Markovič M, Kandríková B, Gracza T. Synthesis 2014; 46: 809
- 16 The racemic lactones ido-10/galacto-10 were prepared from (±)-xylo-8/lyxo-8 in a parallel synthesis.