Siklohekzen ve Siklohekzadienlerden Bromosiklitollerin Sentezi
Year 2024,
, 51 - 58, 23.11.2024
Hülya Çelik
,
Süleyman Göksu
,
Hasan Seçen
Abstract
Siklitoller, önemli biyolojik aktiviteleri nedeniyle yoğun şekilde araştırılan bileşiklerdir. Bu çalışmada, siklohekzen, 1,3-siklohekzadien ve 1,4-siklohekzadien temel alınarak yeni bromosiklitol analoglarının sentezi gerçekleştirildi. cis-Hidroksilleme, asetilleme ve alilik bromlama reaksiyonları ile siklitol analoğu ürünler elde edildi. Elde edilen ürünlerin yapıları aydınlatıldı ve oluşum mekanizmaları detaylı bir şekilde tartışıldı.
References
- 1. Kübler K, Chemistry of condurango bark. Arch Pharm. 1909; 246, 620-660.
- 2. Dangschat G, Fischer HOL. Über die konstitution des condurits und über einige Cyclohexan-tetrole. Naturwissenschaften. 1939; 27: 756-757.
- 3. Kindl H, Hoffmann-Ostenhof O, Cyclites: biosynthesis, metabolism, and occurrence. Fortschrit Chem Organ Naturst. 1966; 24:149.
- 4. Plouvier V. A new cyclitol, leucanthemitol, isolated from Chrysanthemum leucanthemum. Studies on some other anthemia. Compt Rend hebd Se’Acad Sci Paris. 1962; 255:360-362.
- 5. Balcı M, Sütbeyaz Y, Seçen H, Conduritols and related compounds. Tetrahedron. 1990; 46:3715-3742.
- 6. Ramanathan, JD, Craigie JS, McLachlan J, et al. The occurrence of D-(+)-1425-cyclohexanetetrol in Monochrysis lutheri droop. Tetrahedron Lett. 1966; 7: 1527-1531.
- 7. Craigie JS, McLachlan, J, Tocher RD. Some neutral constituents of the Rhodophyceae with special reference to the occurrence of the floridosides. Can J Bot. 1968; 46:605-611.
- 8. Zhang Z, Zhang M. Crystal and molecular structure of natural product toxocarol. Jiegou Huaxue (J. Struc. Chem.) 1987; 6:128-131. Chem Abstr. 1988, 108:167846.
- 9. Legler G. Glucosidases. In: Methods in Enzymology. Academic Press, 1977; 368-381.
- 10. Kensho L, Yamashita F, Nagai T, et al. Use of conduritol to inhibit increase of blood sugar level. Eur.Pat. Appl. EP, 474, 358, 1990, Chem. Abstr. 116:248434.
- 11. Pulverer G, Beuth J, Ko, HL, et al. Glycoprotein modifications of sarcoma L-1 tumor cells by tunicamycin, swainsonine, bromoconduritol or 1-desoxynojirimycin treatment inhibits their metastatic lung colonization in Balb/c-mice. J Cancer Res Clin Oncol. 1988, 114:217-220.
- 12. Datema R, Romero PA, Legler, G, et al. Inhibition of formation of complex oligosaccharides by the glucosidase ınhibitor bromoconduritol. Proc Natl Acad Sci USA. 1982; 79:6787-6791
- 13. Datema R, Romero A, Rott R, et al. On the role of oligosaccharide trimming in the maturation of Sindbis and influenza virus. Arch Virol. 1984 ; 81:25-39.
- 14. Trudel, GC, Herscovics AH, Paul C. Inhibition of myoblast fusion by bromoconduritol. Biochem Cell Biol. 1988; 66:1119-1125.
- 15. Montefiori DC; Robinson Jr WE, Mitchell WM. Antibody-independent, complement-mediated enhancement of HIV-1 infection by mannosidase I and II inhibitors. Antiviral Res. 1989; 11:137-146.
- 16. Silber AM, Candurra NA, Damonte EB. The effects of oligosaccharide trimming inhibitors on glycoprotein expression and infectivity of Junin vırus. FEMS Microbial Lett. 1993, 109:39-43.
- 17. Guo ZX, Haines AH, Taylor, RJK. The reaction of dilithium tetrachlorocuprate and dilithium tetrabromonickelate with unsaturated epoxides - the preparation of novel analogs of the antıviral agent, bromoconduritol. Synlett. 1993; 607-608.
- 18. Baran A, Kazaz C, Seçen H, Sütbeyaz Y. Synthesis of haloconduritols from an endo cycloadduct of furan and vinylene carbonate. Tetrahedron. 2003; 59: 3643–3648.
- 19. Langlois JB, Alexakis, A. Copper‐catalyzed asymmetric allylic alkylation of racemic cyclic substrates: application of dynamic kinetic asymmetric transformation (DYKAT). Adv Synth Catal. 2010; 352(2‐3): 447-457.
- 20. Alvarez E; Nunez MT; Martin, VS. Mild and stereocontrolled synthesis of iodo-and bromohydrins by halogen-tetrakis (isopropoxy) titanium opening of epoxy alcohols. J Org Chem. 1990; 55:3429-3431.
- 21. Tschamber T, Backenstrass F, Fritz, H et al. (1992). Catalytic one-pot osmylation of cyclohexadienes: Stereochemical and conformational studies of the resulting polyols. Helv Chim Acta. 1992, 75:1052-1060.
- 22. Selander, N, Szabo, KJ. Synthesis of stereodefined substituted cycloalkenes by a one-pot catalytic boronation–allylation–metathesis sequence. Adv Synth Catal. 2008; 350:2045-2051.
- 23. Donohoe, T J, Mitchell, L, & Waring, M J, et al. Scope of the directed dihydroxylation: Application to cyclic homoallylic alcohols and trihaloacetamides. Org Biomol Chem. 2003, 1:2173-2186.
- 24. Laserna V, Fiorani, G, Whiteoak, CJ, et al. Carbon dioxide as a protecting group: Highly efficient and selective catalytic access to cyclic cis-diol scaffolds. Angew Chem Int Ed. 2014; 53: 10416-10419.
- 25. Uemura S, Ohe K, Fukuzawa S, et al. Dominant cis-diacetoxylation of alkenes with tellurium(IV) oxide and lithium bromide in acetic acid. J Organomet Chem. 1986; 316:67-78.
- 26. Wohl–Ziegler bromination. (n.d.). In Wikipedia. Erişim September 30, 2024, from https://en.wikipedia.org/wiki/WohlZiegler_bromination
- 27. Van Rheen V, Cha, DY, Hartley, WM. Catalytic osmium tetroxide oxidation of olefins: cis-1,2-cyclohexanediol. Org Synt Coll Vol. 1988; 6:342.
Syntheses of Bromocyclitos via Cyclohexene and Cyclohexadienes
Year 2024,
, 51 - 58, 23.11.2024
Hülya Çelik
,
Süleyman Göksu
,
Hasan Seçen
Abstract
Cyclitols are compounds that have been intensively researched due to their important biological activities. In this study, new bromocyclitol analogues were synthesized based on cyclohexene, 1,3-cyclohexadiene and 1,4-cyclohexadiene. Cyclitol analogues were obtained by cis-hydroxylation, acetylation and allylic bromination reactions. The structures of the obtained products were elucidated and their formation mechanisms were discussed in detail.
References
- 1. Kübler K, Chemistry of condurango bark. Arch Pharm. 1909; 246, 620-660.
- 2. Dangschat G, Fischer HOL. Über die konstitution des condurits und über einige Cyclohexan-tetrole. Naturwissenschaften. 1939; 27: 756-757.
- 3. Kindl H, Hoffmann-Ostenhof O, Cyclites: biosynthesis, metabolism, and occurrence. Fortschrit Chem Organ Naturst. 1966; 24:149.
- 4. Plouvier V. A new cyclitol, leucanthemitol, isolated from Chrysanthemum leucanthemum. Studies on some other anthemia. Compt Rend hebd Se’Acad Sci Paris. 1962; 255:360-362.
- 5. Balcı M, Sütbeyaz Y, Seçen H, Conduritols and related compounds. Tetrahedron. 1990; 46:3715-3742.
- 6. Ramanathan, JD, Craigie JS, McLachlan J, et al. The occurrence of D-(+)-1425-cyclohexanetetrol in Monochrysis lutheri droop. Tetrahedron Lett. 1966; 7: 1527-1531.
- 7. Craigie JS, McLachlan, J, Tocher RD. Some neutral constituents of the Rhodophyceae with special reference to the occurrence of the floridosides. Can J Bot. 1968; 46:605-611.
- 8. Zhang Z, Zhang M. Crystal and molecular structure of natural product toxocarol. Jiegou Huaxue (J. Struc. Chem.) 1987; 6:128-131. Chem Abstr. 1988, 108:167846.
- 9. Legler G. Glucosidases. In: Methods in Enzymology. Academic Press, 1977; 368-381.
- 10. Kensho L, Yamashita F, Nagai T, et al. Use of conduritol to inhibit increase of blood sugar level. Eur.Pat. Appl. EP, 474, 358, 1990, Chem. Abstr. 116:248434.
- 11. Pulverer G, Beuth J, Ko, HL, et al. Glycoprotein modifications of sarcoma L-1 tumor cells by tunicamycin, swainsonine, bromoconduritol or 1-desoxynojirimycin treatment inhibits their metastatic lung colonization in Balb/c-mice. J Cancer Res Clin Oncol. 1988, 114:217-220.
- 12. Datema R, Romero PA, Legler, G, et al. Inhibition of formation of complex oligosaccharides by the glucosidase ınhibitor bromoconduritol. Proc Natl Acad Sci USA. 1982; 79:6787-6791
- 13. Datema R, Romero A, Rott R, et al. On the role of oligosaccharide trimming in the maturation of Sindbis and influenza virus. Arch Virol. 1984 ; 81:25-39.
- 14. Trudel, GC, Herscovics AH, Paul C. Inhibition of myoblast fusion by bromoconduritol. Biochem Cell Biol. 1988; 66:1119-1125.
- 15. Montefiori DC; Robinson Jr WE, Mitchell WM. Antibody-independent, complement-mediated enhancement of HIV-1 infection by mannosidase I and II inhibitors. Antiviral Res. 1989; 11:137-146.
- 16. Silber AM, Candurra NA, Damonte EB. The effects of oligosaccharide trimming inhibitors on glycoprotein expression and infectivity of Junin vırus. FEMS Microbial Lett. 1993, 109:39-43.
- 17. Guo ZX, Haines AH, Taylor, RJK. The reaction of dilithium tetrachlorocuprate and dilithium tetrabromonickelate with unsaturated epoxides - the preparation of novel analogs of the antıviral agent, bromoconduritol. Synlett. 1993; 607-608.
- 18. Baran A, Kazaz C, Seçen H, Sütbeyaz Y. Synthesis of haloconduritols from an endo cycloadduct of furan and vinylene carbonate. Tetrahedron. 2003; 59: 3643–3648.
- 19. Langlois JB, Alexakis, A. Copper‐catalyzed asymmetric allylic alkylation of racemic cyclic substrates: application of dynamic kinetic asymmetric transformation (DYKAT). Adv Synth Catal. 2010; 352(2‐3): 447-457.
- 20. Alvarez E; Nunez MT; Martin, VS. Mild and stereocontrolled synthesis of iodo-and bromohydrins by halogen-tetrakis (isopropoxy) titanium opening of epoxy alcohols. J Org Chem. 1990; 55:3429-3431.
- 21. Tschamber T, Backenstrass F, Fritz, H et al. (1992). Catalytic one-pot osmylation of cyclohexadienes: Stereochemical and conformational studies of the resulting polyols. Helv Chim Acta. 1992, 75:1052-1060.
- 22. Selander, N, Szabo, KJ. Synthesis of stereodefined substituted cycloalkenes by a one-pot catalytic boronation–allylation–metathesis sequence. Adv Synth Catal. 2008; 350:2045-2051.
- 23. Donohoe, T J, Mitchell, L, & Waring, M J, et al. Scope of the directed dihydroxylation: Application to cyclic homoallylic alcohols and trihaloacetamides. Org Biomol Chem. 2003, 1:2173-2186.
- 24. Laserna V, Fiorani, G, Whiteoak, CJ, et al. Carbon dioxide as a protecting group: Highly efficient and selective catalytic access to cyclic cis-diol scaffolds. Angew Chem Int Ed. 2014; 53: 10416-10419.
- 25. Uemura S, Ohe K, Fukuzawa S, et al. Dominant cis-diacetoxylation of alkenes with tellurium(IV) oxide and lithium bromide in acetic acid. J Organomet Chem. 1986; 316:67-78.
- 26. Wohl–Ziegler bromination. (n.d.). In Wikipedia. Erişim September 30, 2024, from https://en.wikipedia.org/wiki/WohlZiegler_bromination
- 27. Van Rheen V, Cha, DY, Hartley, WM. Catalytic osmium tetroxide oxidation of olefins: cis-1,2-cyclohexanediol. Org Synt Coll Vol. 1988; 6:342.