RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2017; 49(07): 1561-1568
DOI: 10.1055/s-0036-1588666
DOI: 10.1055/s-0036-1588666
paper
New and Convenient Chemoenzymatic Syntheses of (S)-2-Hydroxy-3-octanone, the Major Pheromone Component of Xylotrechus spp., and Its R-Enantiomer
Weitere Informationen
Publikationsverlauf
Received: 14. Oktober 2016
Accepted after revision: 11. November 2016
Publikationsdatum:
15. Dezember 2016 (online)
Abstract
New and efficient chemoenzymatic approaches for the synthesis of both enantiomers of 2-hydroxy-3-octanone in good yields and excellent enantioselectivity are presented. The S-enantiomer is a pheromone component of economically important pests in Japan, India, China, and other Asian countries. The enzymatic approaches involve transesterification of the racemic acyloin with vinyl acetate in the presence of Candida antarctica lipase B (CAL B) in 99% ee of both enantiomers (E = 167–618), or hydrolysis of the acetylated acyloin by double kinetic resolution with CAL B and C. antarctica lipase A (CAL A) in 96–98% ee of either enantiomer (E = 458). CAL A and CAL B induce reverse enantioselectivity.
Key words
pheromones - biocatalysis - chiral resolution - enzymes - 2-hydroxy 3-ketones - enantioselectivitySupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588666 and contains experimental details for the intermediates in the synthesis of acyloin (±)-1 and copies of the 1H and 13C NMR spectra for new compounds and intermediates.
- Supporting Information
-
References
- 1 Hoyos P, Sinisterra J.-V, Molinari F, Alcántara AR, Domínguez de María P. Acc. Chem. Res. 2010; 43: 288
- 2a Hanessian S. Total Synthesis of Natural Products: The Chiron Approach. Pergamon Press; New York: 1983
- 2b Masamune S, Choy W, Petersen JS, Sita LR. Angew. Chem., Int. Ed. Engl. 1985; 24: 1
- 2c Oppolzer W. Angew. Chem., Int. Ed. Engl. 1984; 23: 876
- 2d Reetz MT. Angew. Chem., Int. Ed. Engl. 1984; 23: 556
- 3a Bogevig A, Sunden H, Cordova A. Angew. Chem. Int. Ed. 2004; 43: 1109
- 3b Davis FA, Chen BC. Chem. Rev. 1992; 92: 919
- 3c Plietker B. Eur. J. Org. Chem. 2005; 1919
- 4a Alamsetti SK, Muthupandi P, Sekar G. Chem. Eur. J. 2009; 15: 5424
- 4b Muthupandi P, Alamsetti SK, Sekar G. Chem. Commun. 2009; 3288
- 5a Onomura O, Arimoto H, Matsumura Y, Demizu Y. Tetrahedron Lett. 2007; 48: 8668
- 5b Zhang JD, Xu TT, Li Z. Adv. Synth. Catal. 2013; 355: 3147
- 6a Adam W, Díaz MT, Fell RT, Saha-Möller CR. Tetrahedron: Asymmetry 1996; 7: 2207
- 6b Agudo R, Roiban G.-D, Lonsdale R, Ilie A, Reetz MT. J. Org. Chem. 2015; 80: 950
- 6c Molinari F. Curr. Org. Chem. 2006; 10: 1247
- 6d Petrenz A, Domínguez de María P, Ramanathan A, Hanefeld U, Ansorge-Schumacher MB, Kara S. J. Mol. Catal. B: Enzym. 2015; 114: 42
- 6e Tanyeli C, Akhmedov I, Iyigun C. Tetrahedron: Asymmetry 2006; 17: 1125
- 7 Hoyos P, Fernandez M, Sinisterra J.-V, Alcántara AR. J. Org. Chem. 2006; 71: 7632
- 8a Adam W, Díaz MT, Saha-Möller CR. Tetrahedron: Asymmetry 1998; 9: 791
- 8b Scheid G, Ruijter E, Konarzycka-Bessler M, Bornscheuer UT, Wessjohann LA. Tetrahedron: Asymmetry 2004; 15: 2861
- 9 Scheid G, Kuit W, Ruijter E, Orru RV. A, Henke E, Bornscheuer U, Wessjohann LA. Eur. J. Org. Chem. 2004; 1063
- 10 Bortolini O, Fantin G, Fogagnolo M, Giovannini PP, Guerrini A, Medici A. J. Org. Chem. 1997; 62: 1854
- 11 Nakamura K, Kondo S, Kawai Y, Hida K, Kitano K, Ohno A. Tetrahedron: Asymmetry 1996; 7: 409
- 12a Iwabuchi K, Takahashi J, Nakagawa Y, Sakai T. Appl. Entomol. Zool. 1986; 21: 21
- 12b Sakai T, Nakagawa Y, Takahashi J, Iwabuchi K, Ishii K. Chem. Lett. 1984; 263
- 13 Kuwahara Y, Matsuyama S, Suzuki T. Appl. Entomol. Zool. 1987; 22: 25
- 14 Hall DR, Cork A, Phythian SJ, Chittamuru S, Jayarama BK, Venkatesha MG, Sreedharan K, Vinod Kumar PK, Seetharama HG, Naidu R. J. Chem. Ecol. 2006; 32: 195
- 15 Mori K, Otsuka T. Tetrahedron 1985; 41: 553
- 16 Kawai Y, Hida K, Tsujimoto M, Kondo S, Kitano K, Nakamura K, Ohno A. Bull. Chem. Soc. Jpn. 1999; 72: 99
- 17 Leal WS, Shi X, Nakamuta K, Ono M, Meinwald J. Proc. Natl. Acad. Sci. U.S.A. 1995; 92: 1038
- 18 Uppenberg J, Oehrner N, Norin M, Hult K, Kleywegt GJ, Patkar S, Waagen V, Anthonsen T, Jones TA. Biochemistry 1995; 34: 16838
- 19a Anderson EM, Karin M, Kirk O. Biocatal. Biotransform. 1998; 16: 181
- 19b Gotor-Fernández V, Busto E, Gotor V. Adv. Synth. Catal. 2006; 348: 797
- 19c Orrenius C, Norin T, Hult K, Carrea G. Tetrahedron: Asymmetry 1995; 6: 3023
- 19d Persson BA, Larsson AL. E, Le Ray M, Bäckvall J.-E. J. Am. Chem. Soc. 1999; 121: 1645
- 20 Hall DR, Amarawardana L, Cross JV, Francke W, Boddum T, Hillbur Y. J. Chem. Ecol. 2012; 38: 2
- 21 Domínguez de María P, Carboni-Oerlemans C, Tuin B, Bargeman G, van der Meer A, van Gemert R. J. Mol. Catal. B: Enzym. 2005; 37: 36
- 22 Kirk O, Christensen MW. Org. Process Res. Dev. 2002; 6: 446
- 23 Martinelle M, Holmquist M, Hult K. Biochim. Biophys. Acta 1995; 1258: 272
- 24a de Gonzalo G, Brieva R, Sánchez VM, Bayod M, Gotor V. J. Org. Chem. 2001; 66: 8947
- 24b de Gonzalo G, Brieva R, Sánchez VM, Bayod M, Gotor V. J. Org. Chem. 2003; 68: 3333
- 25 Lee LG, Whitesides GM. J. Org. Chem. 1986; 51: 25
- 26a Chen CS, Fujimoto Y, Girdaukas G, Sih CJ. J. Am. Chem. Soc. 1982; 104: 7294
- 26b Faber K., Hoenig H. http://biocatalysis.uni-graz.at/enantio/cgi-bin/enantio.pl.
- 27 Kiyota R, Yamakawa R, Iwabuchi K, Hoshino K, Ando T. Biosci., Biotechnol., Biochem. 2009; 73: 2252
- 28 Kajiro H, Mitamura S.-i, Mori A, Hiyama T. Synlett 1998; 51
- 29 Demir AS, Sesenoglu O. Org. Lett. 2002; 4: 2021
- 30 Ma L.-Y, Liu W.-Z, Shen L, Huang Y.-L, Rong X.-G, Xu Y.-Y, Gao X.-D. Tetrahedron 2012; 68: 2276