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Synthesis of New Medium- and Large- Sized Racemic and Chiral Lactones

Yıl 2018, Cilt: 5 Sayı: 2, 539 - 550, 01.01.2018

Hasniye Yaşa Ayşe Sergüzel Yusufoğlu

https://doi.org/10.18596/jotcsa.372628
Cited By: 1

Öz

Successive
reaction of long chain w-1, w-2, w-4 and w-5 hydroxycarboxylic acids 1a-1e with a cyanuric chloride (CC) and
triethylamine afforded the corresponding racemic lactones 2a-2e in high yields. Optically pure R lactones 4a-4e were
synthesized stereoselectively by porcine pancreas lipase-catalysed resolution
of racemic 2a-2e. The resolution
conditions were investigated, determined and optical rotations were measured.
The mentioned chiral lactones were synthesized by this method for the first
time. The obtained racemic and chiral lactones were analysed by NMR, IR, Mass,
optical rotation and C,H analysis.

Anahtar Kelimeler

Synthesis medium and large ring lactone

Kaynakça

  • 1. Siegel SM. Inhibitory activity of the phenolic glucoside psilotin and its several by gibberellic acid and thiols. Phytochem. 1976 15: 566-567. DOI: org/10.1016/S0031-9422(00)88980-3.
  • 2. Ohloff G. Recent developments in the field of naturally occurring aroma components. Prog. Chem. Org. Nat. Prod. 1978 35: 431-527. DOI: org/10.1007/978-3-7091-8505-6_5.
  • 3. Davies-Coleman MT, Rivett DEA. Naturally occurring 6-substituted 5,6-dihydro-α-pyrones. Chem. Org. Nat. 1989 55: 1-35. DOI: org/10.1007/978-3-7091-9002-9_1.
  • 4. Fukusaki E, Senda S, Nakazono Y, Omata T. Lipase-catalyzed kinetic resolution of methyl 4-hydroxy-5-tetradecynoate and its application to a facile synthesis of Japanese beetle pheromeno. Tetrahedron 1991 47: 6223-6230. DOI: org/10.1016/S0040-4020(01)86554-6.
  • 5. Mori K. Synthesis of optically active pheromenos. Tetrahedron 1989 45: 3233-3298. DOI: org/10.1016/S0040-4020(01)81007-3.
  • 6. Fujita T, Nishimura H, Kaburagi K, Mizutani J. Plant-growth-inhibiting α-pyrones from Alpina spiciosa. Phytochem. 1994 36: 23-27. DOI: org/10.1016/S0031-9422(00)97005-5.
  • 7. Nyandat E, Rwekika E, Galeffi C, Palazzino G, Nicoletti M. Olinioside,5-(4’-O-β-D-glucopyranosyl)-caffeoyloxy-5,6-dihydro-4-methyl-(2H)-pyran-2-one from Olinia usambarensis. Phytochem. 1993 33: 1493-1496. DOI: org/10.1016/0031-9422(93)85118-B.
  • 8. Adrianaivoravelona JO, Sahpaz S, Terreaux C, Hostettmann K, Stoeckli-Evans H, Rasolondramanitra H. Two 6-substituted 5,6-dihydro-α-pyrones from Ravensara anisata. Phytochem. 1999 52: 265-269. DOI: org/10.1016/S0031-9422(99)00158-2.
  • 9. Pereda-Miranda R, Garcia M, Delgado G. Structure and stereochemistry of four α-pytones from Hyptis oblongifolia. Phytochem., 1990 29: 2971-2974. DOI: org/10.1016/0031-9422(90)87117-D
  • 10. Nicolaou KC, Rodrigues RM, Mitchell HJ, Suzuki H, Fylaktakidou KC, Baudoin O, van Delft FL. Total synthesis of everninimicin 13,384-1, part 1: Retrosynthetic analysis of the A1B(A)C fragment. Chem. Eur. J, 2000 6: 3095-3115. DOI:10.1002/(SICI)1521-3773.
  • 11. Jodynis-Liebert J, Murias M, Bloszyk E. Effect of sesquiterpene lactones and antioxidant enzymes and some drug-metabolizing enzymes in rat liver and kidney. Planta Med. 2009 66: 199-205. DOI: 10.1055/s-2000-8566.
  • 12. Drewes SE, Schlapelo BM, Horn MM, Scott-Shaw V, Sandor O. 5,6-Dihydro-α-pyrones and two bicyclic tetrahydro-α-pyrone derivatives from Cryptocarya latifolia. Phytochem. 1995 38: 1427-1430. DOI: org/10.1080/00397911.2010.529230.
  • 13. (a) Drauz K, Waldmann H. Enzyme Catalysis in Organic Synthesis. VCH: Weinheim, 1995. DOI: 10.1002/9783527619429.ch1. (b) Bornscheuer UT, Kazlauskas RJ. Hydrolases in Organic Synthesis, Wiley- VCH: Weinheim, 1999. DOI: 10.1002/3527607544.ch7.
  • 14. Boden EP, Keck GE. Proton-transfer steps in Steglich esterification: a very practical new method for macrolactonization, J.Org.Chem. 1985 50: 2394. DOI: 10.1021/jo00213a044.
  • 15. Inanaga J, Hirata K, Saeki L, Katsuki T, Yamaguchi M. A rapid esterification by mixed anhydride and its application to large-ring lactonization. Bull. Chem. Soc. Jpn. 1979 52: 1989. DOI: org/10.1246/bcsj.52.1989.
  • 16. Corey EJ, Nicolaou KC. Efficient and mild lactonization method for the synthesis of macrolides. J.Am.Chem.Soc. 1974 96: 5614-5616. DOI: 10.1021/ja00824a073.
  • 17. Mukaiyama T, Usui M, Saigo K. The facile synthesis of lactones. Chem. Lett. 1976 5: 49-50. DOI: org/10.1246/cl.1976.49.
  • 18. Shiina I, Kubota M, Ibuka R. A novel and efficient macrolactonization of ω-hydroxycarboxylic acids using 2-methyl-6-nitrobenzoic anhydride (MNBA). Tetrahedron Lett. 2002 43: 7535-7539. DOI:org/10.1016/S0040-4039(02)01819-1.
  • 19. Shiina I, Kubota M, Oshiumi H, Hashizume M. An Effective Use of Benzoic Anhydride and Its Derivatives for the Synthesis of Carboxylic Esters and Lactones:  A Powerful and Convenient Mixed Anhydride Method Promoted by Basic Catalysts. J.Org.Chem. 2004 69: 1822-1830. DOI: 10.1021/jo030367x.
  • 20. Venkataraman K, Wagle DR. Cyanuric chloride, a useful reagent for macrocyclic lactonization. Tetrahedron Lett. 1980 21: 1893-1896. DOI: org/10.1016/S0040-4039(00)92809-0.
  • 21. Cossy J, Peten JP. A three step synthesis of exaltolide and phoracantholide I. Tetrahedron Lett. 1986 27: 2369-2370. DOI: org/10.1016/S0040-4039(00)84531-1
  • 22. Cossy J, Pete JP. Synthesis of medium-ring lactones: Application to the synthesis of 15-pentadecanolide and phoracantholide I. Bull. Soc. Chim.Fr. 1988 6: 989-994. CODEN: BSCFAS; ISSN: 0037-8968; French
  • 23. Ayyangar NR, Chanda B, Wakharkar RD, Kasar RA. A short convergent synthesis of Patulolide A. Synth.Commun. 1988 18: 2103-2019. DOI: org/10.1080/00397918808068279.
  • 24. Hinkamp L, Schaefer H, Wippich B, Luftmann H. Regioselective conversion of nonactivated carbon-hydrogen bonds. VI. Selective ω- to (ω-2)-chlorination of fatty acids via adsorption on alümina. Liebigs Annalen der Chemie 1992 6: 559-63
  • 25. Noda Y, Kashin H. Synthesis of Both Enantiomers of Four Different Macrocyclic Lactones. Heterocycles 1998 48: 5-10. DOI: 10.3987/COM-97-7991.
  • 26. Stanchev S, Hesse M. Synthesis of the enantiomerically enriched macrocyclic lactones (+)-(S)- and (-)-(R)-phorocantholide I and (+)-(S)-tetradecan-13-olide. Helv. Chim. Acta 1990 73: 460-467. DOI: 10.1002/hlca.19900730226.
  • 27. Bestmann H.J, Kellermann W. Synthese der natürlichen R-( - )Enantiomere dreier Galbanum-Harz Macrolide. Synthesis 1994 12: 1257-1261. DOI: 10.1055/s-1994-25676.
  • 28. Kaiser R, Lamparsky D. Neue Macrolide und einige sesquiterpen-derivative aus dem Galbanum-Harz. Helv.Chim.Acta. 1978 61: 2671/2680. DOI: 10.1002/hlca.19780610736.
  • 29. Bollbuck B, Kraft P, Tochtermann W. Nature-like odorants by stereoselective ring enlargement of cyclohexanone and cyclododecanone. Tetrahedron 1996 52: 4581-4592. DOI: org/10.1016/0040-4020(96)00170-6.
  • 30. Siedle B, Gustavsson L, Johansson S, Murillo R, Castro V, Bohlin V, Merfat I. The effect of sesquiterpene lactones on the release of human neutrophil elastase. Biochem. Pharmacol. 2003 65: 897-903. DOI: org/10.1016/S0006-2952(02)01652-0.
  • 31. Dou D, He G, Li Y, Lai Z, Wei L, Alliston KR, Lushington GH, Eichhorn DM, Groutas WC. Utilization of the 1,2,3,5-thiatriazolidin-3-one 1,1-dioxide scaffold in the design of potential inhibitors of human neutrophil proteinase 3. Bioorg. Med. Chem. 2010 18: 1093-1102. DOI: org/10.1016/j.bmc.2009.12.057.
  • 32. Baspinar Kücük H, Yusufoglu A. Enantioselective synthesis of 3-hydroxytetradecanoic acid and its methyl ester enantiomers as new antioxidants and enzyme inhibitors. Monatsh Chem. 2013 144: 1087-1091. DOI:10.1007/s00706-012-0917-z.
  • 33. Blaise EE. Blaise Reactions. C.R.Hebd. Seacens Acad. Sci. 1913 157: 1440
  • 34. Stenhagen SS, Stenhagen E. Synthesis of higher beta keto acids with 9 to 24 carbon atoms. Arkiv Kemi Mineral Geol. A 1945 A20: No:19.
  • 35. Yanardağ R, Bapçum A. Chim Acta Turc. 1996 24: 15.

Yıl 2018, Cilt: 5 Sayı: 2, 539 - 550, 01.01.2018

Hasniye Yaşa Ayşe Sergüzel Yusufoğlu

https://doi.org/10.18596/jotcsa.372628
Cited By: 1

Öz

Kaynakça

  • 1. Siegel SM. Inhibitory activity of the phenolic glucoside psilotin and its several by gibberellic acid and thiols. Phytochem. 1976 15: 566-567. DOI: org/10.1016/S0031-9422(00)88980-3.
  • 2. Ohloff G. Recent developments in the field of naturally occurring aroma components. Prog. Chem. Org. Nat. Prod. 1978 35: 431-527. DOI: org/10.1007/978-3-7091-8505-6_5.
  • 3. Davies-Coleman MT, Rivett DEA. Naturally occurring 6-substituted 5,6-dihydro-α-pyrones. Chem. Org. Nat. 1989 55: 1-35. DOI: org/10.1007/978-3-7091-9002-9_1.
  • 4. Fukusaki E, Senda S, Nakazono Y, Omata T. Lipase-catalyzed kinetic resolution of methyl 4-hydroxy-5-tetradecynoate and its application to a facile synthesis of Japanese beetle pheromeno. Tetrahedron 1991 47: 6223-6230. DOI: org/10.1016/S0040-4020(01)86554-6.
  • 5. Mori K. Synthesis of optically active pheromenos. Tetrahedron 1989 45: 3233-3298. DOI: org/10.1016/S0040-4020(01)81007-3.
  • 6. Fujita T, Nishimura H, Kaburagi K, Mizutani J. Plant-growth-inhibiting α-pyrones from Alpina spiciosa. Phytochem. 1994 36: 23-27. DOI: org/10.1016/S0031-9422(00)97005-5.
  • 7. Nyandat E, Rwekika E, Galeffi C, Palazzino G, Nicoletti M. Olinioside,5-(4’-O-β-D-glucopyranosyl)-caffeoyloxy-5,6-dihydro-4-methyl-(2H)-pyran-2-one from Olinia usambarensis. Phytochem. 1993 33: 1493-1496. DOI: org/10.1016/0031-9422(93)85118-B.
  • 8. Adrianaivoravelona JO, Sahpaz S, Terreaux C, Hostettmann K, Stoeckli-Evans H, Rasolondramanitra H. Two 6-substituted 5,6-dihydro-α-pyrones from Ravensara anisata. Phytochem. 1999 52: 265-269. DOI: org/10.1016/S0031-9422(99)00158-2.
  • 9. Pereda-Miranda R, Garcia M, Delgado G. Structure and stereochemistry of four α-pytones from Hyptis oblongifolia. Phytochem., 1990 29: 2971-2974. DOI: org/10.1016/0031-9422(90)87117-D
  • 10. Nicolaou KC, Rodrigues RM, Mitchell HJ, Suzuki H, Fylaktakidou KC, Baudoin O, van Delft FL. Total synthesis of everninimicin 13,384-1, part 1: Retrosynthetic analysis of the A1B(A)C fragment. Chem. Eur. J, 2000 6: 3095-3115. DOI:10.1002/(SICI)1521-3773.
  • 11. Jodynis-Liebert J, Murias M, Bloszyk E. Effect of sesquiterpene lactones and antioxidant enzymes and some drug-metabolizing enzymes in rat liver and kidney. Planta Med. 2009 66: 199-205. DOI: 10.1055/s-2000-8566.
  • 12. Drewes SE, Schlapelo BM, Horn MM, Scott-Shaw V, Sandor O. 5,6-Dihydro-α-pyrones and two bicyclic tetrahydro-α-pyrone derivatives from Cryptocarya latifolia. Phytochem. 1995 38: 1427-1430. DOI: org/10.1080/00397911.2010.529230.
  • 13. (a) Drauz K, Waldmann H. Enzyme Catalysis in Organic Synthesis. VCH: Weinheim, 1995. DOI: 10.1002/9783527619429.ch1. (b) Bornscheuer UT, Kazlauskas RJ. Hydrolases in Organic Synthesis, Wiley- VCH: Weinheim, 1999. DOI: 10.1002/3527607544.ch7.
  • 14. Boden EP, Keck GE. Proton-transfer steps in Steglich esterification: a very practical new method for macrolactonization, J.Org.Chem. 1985 50: 2394. DOI: 10.1021/jo00213a044.
  • 15. Inanaga J, Hirata K, Saeki L, Katsuki T, Yamaguchi M. A rapid esterification by mixed anhydride and its application to large-ring lactonization. Bull. Chem. Soc. Jpn. 1979 52: 1989. DOI: org/10.1246/bcsj.52.1989.
  • 16. Corey EJ, Nicolaou KC. Efficient and mild lactonization method for the synthesis of macrolides. J.Am.Chem.Soc. 1974 96: 5614-5616. DOI: 10.1021/ja00824a073.
  • 17. Mukaiyama T, Usui M, Saigo K. The facile synthesis of lactones. Chem. Lett. 1976 5: 49-50. DOI: org/10.1246/cl.1976.49.
  • 18. Shiina I, Kubota M, Ibuka R. A novel and efficient macrolactonization of ω-hydroxycarboxylic acids using 2-methyl-6-nitrobenzoic anhydride (MNBA). Tetrahedron Lett. 2002 43: 7535-7539. DOI:org/10.1016/S0040-4039(02)01819-1.
  • 19. Shiina I, Kubota M, Oshiumi H, Hashizume M. An Effective Use of Benzoic Anhydride and Its Derivatives for the Synthesis of Carboxylic Esters and Lactones:  A Powerful and Convenient Mixed Anhydride Method Promoted by Basic Catalysts. J.Org.Chem. 2004 69: 1822-1830. DOI: 10.1021/jo030367x.
  • 20. Venkataraman K, Wagle DR. Cyanuric chloride, a useful reagent for macrocyclic lactonization. Tetrahedron Lett. 1980 21: 1893-1896. DOI: org/10.1016/S0040-4039(00)92809-0.
  • 21. Cossy J, Peten JP. A three step synthesis of exaltolide and phoracantholide I. Tetrahedron Lett. 1986 27: 2369-2370. DOI: org/10.1016/S0040-4039(00)84531-1
  • 22. Cossy J, Pete JP. Synthesis of medium-ring lactones: Application to the synthesis of 15-pentadecanolide and phoracantholide I. Bull. Soc. Chim.Fr. 1988 6: 989-994. CODEN: BSCFAS; ISSN: 0037-8968; French
  • 23. Ayyangar NR, Chanda B, Wakharkar RD, Kasar RA. A short convergent synthesis of Patulolide A. Synth.Commun. 1988 18: 2103-2019. DOI: org/10.1080/00397918808068279.
  • 24. Hinkamp L, Schaefer H, Wippich B, Luftmann H. Regioselective conversion of nonactivated carbon-hydrogen bonds. VI. Selective ω- to (ω-2)-chlorination of fatty acids via adsorption on alümina. Liebigs Annalen der Chemie 1992 6: 559-63
  • 25. Noda Y, Kashin H. Synthesis of Both Enantiomers of Four Different Macrocyclic Lactones. Heterocycles 1998 48: 5-10. DOI: 10.3987/COM-97-7991.
  • 26. Stanchev S, Hesse M. Synthesis of the enantiomerically enriched macrocyclic lactones (+)-(S)- and (-)-(R)-phorocantholide I and (+)-(S)-tetradecan-13-olide. Helv. Chim. Acta 1990 73: 460-467. DOI: 10.1002/hlca.19900730226.
  • 27. Bestmann H.J, Kellermann W. Synthese der natürlichen R-( - )Enantiomere dreier Galbanum-Harz Macrolide. Synthesis 1994 12: 1257-1261. DOI: 10.1055/s-1994-25676.
  • 28. Kaiser R, Lamparsky D. Neue Macrolide und einige sesquiterpen-derivative aus dem Galbanum-Harz. Helv.Chim.Acta. 1978 61: 2671/2680. DOI: 10.1002/hlca.19780610736.
  • 29. Bollbuck B, Kraft P, Tochtermann W. Nature-like odorants by stereoselective ring enlargement of cyclohexanone and cyclododecanone. Tetrahedron 1996 52: 4581-4592. DOI: org/10.1016/0040-4020(96)00170-6.
  • 30. Siedle B, Gustavsson L, Johansson S, Murillo R, Castro V, Bohlin V, Merfat I. The effect of sesquiterpene lactones on the release of human neutrophil elastase. Biochem. Pharmacol. 2003 65: 897-903. DOI: org/10.1016/S0006-2952(02)01652-0.
  • 31. Dou D, He G, Li Y, Lai Z, Wei L, Alliston KR, Lushington GH, Eichhorn DM, Groutas WC. Utilization of the 1,2,3,5-thiatriazolidin-3-one 1,1-dioxide scaffold in the design of potential inhibitors of human neutrophil proteinase 3. Bioorg. Med. Chem. 2010 18: 1093-1102. DOI: org/10.1016/j.bmc.2009.12.057.
  • 32. Baspinar Kücük H, Yusufoglu A. Enantioselective synthesis of 3-hydroxytetradecanoic acid and its methyl ester enantiomers as new antioxidants and enzyme inhibitors. Monatsh Chem. 2013 144: 1087-1091. DOI:10.1007/s00706-012-0917-z.
  • 33. Blaise EE. Blaise Reactions. C.R.Hebd. Seacens Acad. Sci. 1913 157: 1440
  • 34. Stenhagen SS, Stenhagen E. Synthesis of higher beta keto acids with 9 to 24 carbon atoms. Arkiv Kemi Mineral Geol. A 1945 A20: No:19.
  • 35. Yanardağ R, Bapçum A. Chim Acta Turc. 1996 24: 15.
Toplam 35 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Kimya Mühendisliği
Bölüm Makaleler
Yazarlar

Hasniye Yaşa

Ayşe Sergüzel Yusufoğlu

Yayımlanma Tarihi 1 Ocak 2018
Gönderilme Tarihi 29 Aralık 2017
Kabul Tarihi 16 Mart 2018
Yayımlandığı Sayı Yıl 2018 Cilt: 5 Sayı: 2

Kaynak Göster

Vancouver Yaşa H, Yusufoğlu AS. Synthesis of New Medium- and Large- Sized Racemic and Chiral Lactones. JOTCSA. 2018;5(2):539-50.

Cited By

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 Kapak Resmi İndir
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