Polyhydroxylated carbobicyclic sugar mimics. part 1. synthesis of racemic derivatives

Current Organic Chemistry

Volumn 14, Issue 6, 2010, Pages 533-545

  Nowogródzki, Marcin ^a   Jarosz, Słwomir ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

DECALIN; HYDRINDANE; MECHANISTIC ASPECTS; POLYHYDROXYLATED;

EID: 77954911194     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527210790820230     Document Type: Article

References (71)

1. Robina, I.; Moreno-Vargas, A.J.; Carmona, A.T.; Vogel, P. Glycosidase inhibitors as potential HIV entry inhibitors? Curr. Drug Metab., 2004, 5, 329-361.
2. Chapleur, Y. Carbohydrate Mimics. Concepts and Methods. Wiley-VCH: Weinheim, 1998.
3. Ganem, B. Glycomimetics that inhibit carbohydrate metabolis. In: Carbohydrate Mimics. Concepts and Methods, Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1998, pp. 239-258.
4. Tatsuta, K. Total synthesis and chemical design of useful glycosidase inhibitors. In: Carbohydrate Mimics. Concepts and Methods, Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1998, pp. 283-306.
5. [5] Davies, B.G. A silver-lined anniversary of fleet iminosugars: 1984-2009, from DIM to DRAM to LABNAc. Tetrahedron Asymmetry, 2009, 20, 652671.
6. Stütz, A. Iminosugars as glycosidases inhibitors: Norjirmycin and beyond Wiley-VCH: Weinheim, 1999.
7. Compain, P.; Martin, O.R. Iminosugars: from synthesis to therapeutic applications; John Wiley and Sons: Chichester, 2007.
8. Billington, D.C.; Perron-Sierra, F.; Picard, L.; Beaubras, S.; Duhault, J.; Espinal, J.; Challal, S. Conduritols and analogues as insulin modulators. In: Carbohydrate Mimics. Concepts and Methods Chapleur, Y., Ed.; WileyVCH: Weinheim, 1998, pp. 433-442.
9. Legler, G. Glycoside hydrolases: mechanistic information from studies with reversible and irreversible inhibitors. Adv. Carbohydr. Chem. Biochem., 1990, 48, 319-384.
10. Lang, M.; Ziegler, T. Synthesis of both enantiomers of conduritol C tetraacetate and of meso-conduritol D tetraacetate by oxidation of benzoquinone bis(ethylene acetal). Eur. J. Org. Chem. 2007, 768-776 (and references therein).
11. Gültekin, M.S.; Çelik, M.; Balci, M. Cyclitols: Conduritols and related compounds. Curr. Org. Chem., 2004, 8, 1159-1186.
12. Marco-Contelles, J. Cyclohexane epoxides chemistry and biochemistry of (+)-cyclophellitol. Eur. J. Org. Chem., 2001, 1607-1618.
13. Gloster, T.M.; Madsen, R.; Davies, G.J. Structural basis for cyclophellitol inhibition of a -glucosidase. Org. Biomol. Chem., 2007, 5, 444-446.
14. Berridge, M.J.; Irvine, R.F. Inositol trisphosphate, a novel second messenger in cellular signal transduction. Nature, 1984, 312, 315-321.
15. Berridge, M.J.; Irvine, R.F. Inositol phosphates and cell signalling. Nature, 1989, 341, 197-205.
16. Potter, B.V.L. Recent advances in the chemistry and biochemistry of inositol phosphates of biological interest. Nat. Prod. Rep., 1990, 1-24.
17. Berridge, M.J. Inositol trisphosphate and calcium signalling. Nature 1993, 361, 315-325.
18. Potter, B.V.L.; Lampe, D. Chemistry of inositol lipid mediated cellular signalling. Angew. Chem., Int. Ed. Engl., 1995, 34, 1933-1972.
19. Hinterding, K.; Diaz, D.A.; Waldmann, H. Organic synthesis and biological signal transduction. Angew. Chem., Int. Ed. Engl., 1998, 37, 688-749.
20. Arjona, O.; Gomez, A.M.; Lopez, J.C.; Plumet, J. Synthesis and conformational and biological aspects of carbasugars. Chem. Rev., 2007, 107, 1919-2036.
21. Kobayashi, Y. Carbasugars: Synthesis and functions. In: Glycoscience. FraserReid, B.; Tatsuta, K., Eds.; Springer-Verlag: Berlin Heidelberg, 2008, pp. 1915-1998.
22. Michael, J.P. Indolizidine and quinolizidine alkaloids. Nat. Prod. Rep., 1998, 5, 571-594 (and references therein).
23. Bell, A.A.; Pickering, L.; Watson, A.A.; Nash, R.J.; Griffiths, R.C.; Jones, M.G.; Fleet, G.W. J. 2-Hydroxycastanospermines (dihydroxy-Lswainsonines) from octonolactones: Inhibition of naringinase (Lrhamnosidase). Tetrahedron Lett., 1996, 47, 8561-8564.
24. Yoda, H.; Nakajima, T.; Takabe, K. Stereocontrolled synthesis of a trihydroxylated indolizidine alkaloid, 1-deoxycastanospermine. Synlett, 1997, 911-912.
25. Herczegh, P.; Kovacs, I.; Szilagyi, L.; Sztaricskai, F.; Berecibar, A.; Riche, C.; Chiaroni, A.; Olesker A.; Lukacs, G. Cycloaddition reactions of carbohydrate derivatives. Part VI. Quinolizidine analogs of castanospermine. Tetrahedron, 1995, 51, 2969-2978.
26. Pearson, W.H.; Hembre, E.J. Synthesis of tetrahydroxyquinolizidines: ringexpanded analogs of the mannosidase inhibitor swainsonine. J. Org. Chem., 1996, 61, 5537-5545.
27. Mehta, G.; Ramesh, S.S. Polycyclitols. Novel condriutol and carbasugar hybrids as a new class of glycosidase inhibitors. Chem. Commun., 2000, 2429-2430.
28. Mehta, G.; Ramesh, S.S. Polycyclitols: Synthesis of novel carbasugar and condutitol analogues as potential glycosidase inhibitors. Tetrahedron Lett., 2001, 42, 1987-1990.
29. Mehta, G.; Ramesh, S.S. Polycyclitols: Novel conduritol and carbasugar hybrids as new glycosidase inhibitors. Can. J. Chem., 2005, 83, 581-594.
30. Whalley, H.A.; Chidester, C.G.; Miszak, S.A.; Wnuk, R.J. Nodusmicin: The structure of a new antibiotic. Tetrahedron Lett., 1980, 21, 3659-3662.
31. Dräger, G.; Kirschning, A.; Thiericke, R.; Zerlin, M. Decanolides, 10membered lactones of natural origin. Nat. Prod. Rep., 1996, 13, 365-375.
32. Roush, W.R.; Koyama, K.; Curtin, M.L.; Moriarty, K.J. Studies on the synthesis of nargenicin A1: Highly stereoselective synthesis of the complete carbon framework via the transannular diels alder reaction of an 18membered macrolide. J. Am. Chem. Soc., 1996, 118, 7502-7512.
33. Mehta, G.; Ramesh, S.S. Polycyclitols: Stereoselective synthesis of enantiopure polyhydroxylated hydrindanes (annulated carbasugars). Tetrahedron Lett., 1999, 40, 9137-9140.
34. Mehta, G.; Reddy, D.S.; Ramesh, S.S.; Tatu, U. Polycyclitols: Stereoselective synthesis of decalin and diquinane based polyols as potential glycomimics. Tetrahedron Lett., 1999, 40, 9141-9144.
35. Mehta, G.; Ramesh, S.S. Indian Pat. Appl. IN 2000MA00859 A 20071005 (2007).
36. Mehta, G.; Ramesh, S.S. Indian Pat. Appl. 32. Division of Indian Appl. No. 2000 MA 00859 IN 003CH00650 A 20060428 (2006).
37. Mehta, G.; Ramesh, S.S.; Bera, M.K. Novel conformationally locked inositols. From aromatics to annulated cyclitols. Chem. Eur. J., 2003, 9, 2264-2272.
38. Mehta, G.; Ramesh, S.S. A New Glucose: Towards conformationally locked hexoses through annulations. Eur. J. Org. Chem., 2005, 2225-2238.
39. Forman, M.A.; Dailey, W.P. Convenient Synthesis of the 1,4-bishomo-6secoheptaprismane ring system. J. Org. Chem., 1993, 58, 1501-1507.
40. Mehta, G.; Ramesh, S.S. Quest for inosito-inositols: Synthesis of novel, annulated and conformationally locked inositols. Tetrahedron. Lett., 2003, 44, 3105-3108.
41. Mehta, G.; Ramesh, S.S.; Sen, S. Fine tuning the hydrophilic-hydrophobic balance in inositols through annulation: An analysis of the hydrogen-bonded architectures of annulated inositols. CrystEngComm., 2005, 7, 656-663.
42. Mehta, G.; Pujar, S.R.; Ramesh, S.S.; Islam, K. Enantioselective total synthesis of polyoxygentaed cyclohexanoids: (+)-streptol, ent-RKTS-33 and putative "(+)-parasitenone". Identity of parasitenone with (+)-epoxydon. Tetrahedron Lett., 2005, 46, 3373-3376.
43. Mehta, G.; Pallavi, K. From cyclic polyenes to carbohydrates: Synthesis of the hexose sugar -allose and its 2C branched homologue from cyclooctatetraene. Tetrahedron Lett., 2004, 45, 3865-3867.
44. Mehta, G.; Pallavi, K. From hydrocarbons to polyols. Cyclooctatetraene to novel cyclooctitols. Chem. Commun., 2002, 2828-2829.
45. Mehta, G.; Pallavi, K.; Katukojvala, S. Cyclononitols: a flexible synthetic approach towards nine-membered carbasugar analogues. Tetrahedron Lett., 2009, 50, 4519-4522.
46. Mehta, G.; Sen, S.; Venkatesan, K. Additive induced polymorphous behavior of a conformationally locked hexol. CrystEngComm., 2007, 9, 144-151.
47. Mehta, G.; Sen, S.; Ramesh, S.S. Crystal structures of conformationally locked cyclitols: An analysis of hydrogen-bonded architectures and their implications in crystal engineering. Eur. J. Org. Chem., 2007, 3, 423-436.
48. Banwell, M.G.; Ryan, J.H.; Winkler, D.A. Carbocation-mediated rearrangements within [n.m.1]propellane frameworks. Aust. J. Chem., 1991, 44, 593-611.
49. Hückel, W.; Wörffel, U. Reduktionen in flüssigem Ammoniak VII: Hexahydro-naphthalin. Chem. Ber., 1956, 89, 2098-2104.
50. Shani, A.; Sondheimer, F. Unsaturated macrocyclic compounds. LI. 1,6Oxido[10]annulene. J. Am. Chem. Soc., 1967, 89, 6310-6317.
51. Cha, J.K.; Christ, W.J.; Kishi, Y. On stereochemistry of osmium tetroxide oxidation of allylic alcohol systems: empirical rule. Tetrahedron Lett., 1983, 24, 3943-3946.
52. Cha, J.K.; Christ, W.J.; Kishi, Y. On stereochemistry of osmium tetroxide oxidation of allylic alcohol systems: examples. Tetrahedron Lett., 1983, 24, 3947-3950.
53. Cha, J.K.; Christ, W.J.; Kishi, Y. On stereochemistry of osmium tetraoxide oxidation of allylic alcohol systems. Empirical rule. Tetrahedron Lett., 1984, 24, 2247-2255.
54. Donohoe, T.J. Development of the directed dihydroxylation reaction. Synlett, 2002, 1233.
55. Kara, Y.; Balci, M.; Bourne, S.A.; Watson, W.H. Synthesis of new conduritol analogues derived from bicyclooctatriene: Bis-homo-conduritol-D and bis-homoconduritol-F. Tetrahedron Lett., 1994, 35, 3349-3352.
56. Kelebekli, L.; Kara, Y.; Balci, M. Stereospecific synthesis of a new class of compounds: bis-homoconduritol-A, -D, and -F. Carbohydr. Res., 2005, 340, 1940-1948.
57. Kelebekli, L.; Çelik, M.; Sahin, E.; Kara, Y.; Balci, M. Stereospecific synthesis of a new class of aminocyclitol with the conduramine D-2 configuration. Tetrahedron Lett., 2006, 47, 7031-7035.
58. Kara, Y.; Balci, M. A new and stereospecific synthesis of an inositol analogue: bis-homoinositol. Tetrahedron, 2003, 59, 2063-2066.
59. Baran, A.; Balci, M. Synthesis of bicyclo[2.2.2]octane-2,3,5,6,7,8-hexols (bishomoinositols) as new glycisidase inhibitors. J. Org. Chem., 2008, 73, 4370-4375.
60. Billington, D.C.; Perron-Sierra, F.; Picard, L.; Beaubras, S.; Duhault, J.; Espinal, J.; Challal, S. Conduritols and Analogues as Insulin Modulators. In Carbohydrate Mimics. Concepts and Methods Chapleur, Y, Ed.; WileyVCH: Weinheim, 1998, pp. 433-442.
61. Luche, J.L. Lanthanides in organic chemistry. 1. Selective 1,2 reductions of conjugated ketones. J. Am. Chem. Soc., 1978, 100, 2226-2227.
62. Kallmerten, J. The Chemistry of the nargenicin macrolides. In: Studies in natural product chemistry Rahman, A.-U., Ed.; Elsevier Science Publisher: Amsterdam, 1995, pp. 288-311.
63. Gossinger, E.; Graupe, M.; Kratky, C.; Zimmermann, K. Approach towards an EPC synthesis of nodusmicin III. Preparation of the oxygen bridged decalin part of nodusmicin. Tetrahedron, 1997, 53, 3083-3100.
64. Herczegh, P.; Zsely, M.; Szilagy, L.; Bajza, I.; Kovacs, A.; Batta, G.; Bognar, R. Cycloaddition Reactions in Carbohydrate Chemistry, 112 ACS Sympozjum Series, 494, Guliano, R.M., Ed.; 1992.
65. Jones, R.C.F.; Tunnicliffe, J.H. Nargenicin model studiess: dehydrative rearrangement of a dihydroxyoctahydronaphthalene. Tetrahedron Lett., 1985, 26, 5845-5848.
66. Gossinger, E.; Graupe, M. Untersuchungen zur Synthese des Nodusmicin, I: Darstellung von (±)-(1R,5R,6R,7S8R,9R,10R)-5-Acetyl-7,9-dibenzyloxy-10hydroxy-8-methylbicyclo[4.4.0]decan-3-on. Monatsh. Chem., 1993, 124, 965-979.
67. Plata, D.J.; Kallmerten, J. Total synthesis of (+)-18-deoxynargenicin A1. J. Am. Chem. Soc., 1988, 110, 4041-4042.
68. Kallmerten, J. Synthetic studies of the nargenicins: synthesis of the oxabridged octalin nucleus. Tetrahedron Lett., 1984, 25, 2843-2846.
69. Gonzales, A.G.; Jimenez, A.I.; Ravelo, A.G.; Coll, J.; Gonzales, J.A.; Lloria, J. Antifeedant activity of sesquiterpenes from celastraceae. Biochem. Syst. Ecol., 1997, 25, 513-519.
70. Munoz, O.; Penazola, A.; Gonzales, A.G.; Ravelo, A.G.; Bazzocchi, I.L.; Alvarenga, N.L. The celastraceae from latin america chemistry and biological activity. In Studies in Natural Products Chemistry, Rahman, A.-U., Ed.; Elsevier Science Publisher: Amsterdam, 1996, Vol. 18, pp. 739-783.
71. Descoins, Jr. C.; Thanh, G.V.; Boyer, F-D.; Ducrot, P-H.; Descoins, C.; Lallemand, J-Y. Synthesis of polyhydroxylated decalins; a new strategy toward the total synthesis of agarfuran antifeedants. Synlett, 1999, 240-243.