Synthesis and applications of a chiral-oxygenated 3-chloro-3,6-dihydro-2H-pyran obtained under Overman rearrangement conditions

Tetrahedron Letters

Volumn 51, Issue 2, 2010, Pages 277-280

  Montero, Ana ^a,b   Benito, Esperanza ^a   Herradón, Bernardo ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

3,6 Dihydro 2H pyran; Chlorinated carbohydrate; Experimental modulation of the selectivity; Overman rearrangement; Peptide carbohydrate hybrid; Unsaturated sugar

Indexed keywords

3 CHLORO 3,6 DIHYDRO 2H PYRAN; AMIDE; CALPASTATIN; CARBOHYDRATE DERIVATIVE; CHLORIDE; HYDROQUINONE; PYRANOSIDE; TRICHLOROACETIMIDIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CHLORINATION; CHROMATOGRAPHY; DRUG SYNTHESIS; NUCLEAR OVERHAUSER EFFECT; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 71049141318     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.10.136     Document Type: Article

References (65)

1. de Siilva A.P., McCliean C.D., and Moody T.S. In: Atwood J.L., and Steed J.W. (Eds). Encyclopedia of Supramolecular Chemistry (2004), Marcel Dekker, NY 572-578
2. Harmata M. In: Atwood J.L., and Steed J.W. (Eds). Encyclopedia of Supramolecular Chemistry (2004), Marcel Dekker, NY 887-892
3. Steed J.W., Turner D.R., and Wallace K.J. Core Concepts in Supramolecular Chemistry and Nanochemistry (2007), John Wiley and Sons, Chichester
4. Eguchi E. Bioactive Heterocycles II. In: Gupta R.R. (Ed). Topics in Heterocyclic Chemistry Vol. 8 (2007), Springer, Berlin
5. Sugawara K., and Hashiyama T. Tetrahedron Lett. 48 (2007) 3723-3726
6. Pitt W.R., Parry D.M., Perry B.G., and Groom C.R. J. Med. Chem. 52 (2009) 2952-2963
7. For selected examples on the reactivity, synthesis, and applications of carbohydrates, see:. Valverde S., Herradon B., Rabanal R.M., and Martin-Lomas M. Can. J. Chem. 65 (1987) 339-342
8. Valverde S., Martin-Lomas M., Herradon B., and Garcia-Ochoa S. Tetrahedron 43 (1987) 1895-1901
9. Morcuende A., Valverde S., and Herradon B. Synlett (1994) 89-91
10. Herradón B., and Valverde S. Synlett (1995) 599-602
11. Valverde S., Gomez A.M., Hernandez A., Herradon B., and Lopez J.C. J. Chem. Soc., Chem. Commun. (1995) 2005-2006
12. Herradón B., Fenude E., Bao R., and Valverde S. J. Org. Chem. 61 (1996) 1143-1147
13. Mann, E. Ph.D. Thesis, Universidad Autónoma de Madrid, 2002.
14. For a review on Claisen rearrangement in carbohydrate chemistry, see:. Werschkun B., and Thiem J. Top. Curr. Chem. 215 (2001) 293-325
15. Overman L.E. J. Am. Chem. Soc. 96 (1974) 597-599
16. For a review, see:. Majumdar K.C., Bhattacharyya T., Chattopadhyay B., and Sinha B. Synthesis (2009) 2117-2142
17. For applications of Overman rearrangement in carbohydrate chemistry, see:. Takeda K., Kaji E., Konda Y., Sato N., Nakamura H., Miya N., Morizane A., Yanagisawa Y., Akiyama A., Zen S., and Harigaya Y. Tetrahedron Lett. 33 (1992) 7145-7148
18. Yang J., Mercer G.J., and Nguyen H.M. Org. Lett. 9 (2007) 4231-4234
19. Gupta P., and Vankar Y.D. Eur. J. Org. Chem. (2009) 1925-1933
20. For overviews on peptide-carbohydrate hybrids and sugar amino acids, see:. Schweizer F. Angew. Chem., Int. Ed. 41 (2002) 230-253
21. Gruner S.A.W., Locardi E., Lohof E., and Kessler H. Chem. Rev. 102 (2002) 491-514
22. Chakraborti T.K., Srinivasu P., Tadapar S., and Mohan B.K. J. Chem. Sci. 116 (2004) 187-207
23. Chakraborti T.K., Srinivasu P., Tadapar S., and Mohan B.K. Glycoconjugate J. 22 (2005) 83-93
24. Murphy P.V., and Dunne J.L. Curr. Org. Synth. 3 (2006) 403-437
25. Murphy P.V. Eur. J. Org. Chem. (2007) 4177-4187
26. For recent developments, see:. Jockusch R.A., Talbot F.O., Rogers P.S., Simone M.I., Fleet G.W.J., and Simons J.P. J. Am. Chem. Soc. 128 (2006) 16771-16777
27. Sharma G.V.M., Jadhav V.B., Ramakrishna K.V.S., Jayaprakash P., Narsimulu K., Subash V., and Kunwar A.C. J. Am. Chem. Soc. 128 (2006) 14657-14668
28. Paloumbis G., Petrou C., Nock B., Maina T., Pairas G., Tsoungas P., and Cordopatis P. Synthesis (2007) 845-852
29. Chakraborty T.K., Kumar S.U., Mohan B.K., Sarma G.D., Kiran M.U., and Jagadeesh B. Tetrahedron Lett. 48 (2007) 6945-6950
30. Maity P., Zabel M., and Konig B. J. Org. Chem. 72 (2007) 8046-8053
31. Risseeuw M.D.P., Mazurek J., van Langenvelde A., van der Marel G.A., Overkleeft H.S., and Overhand M. Org. Biomol. Chem. 5 (2007) 2311-2314
32. Bughin C., Masson G., and Zhu J. J. Org. Chem. 72 (2007) 1826-1829
33. Chandrasekhar S., Saritha B., Naresh P., Udayakiran M., Reddy C.R., and Jagadeesh B. Helv. Chim. Acta 91 (2008) 1267-1276
34. Tuin A.W., Palachanis D.K., Buizert A., Grotenbreg G.M., Spalburg E., de Neeling A.J., Mars-Groenendijk R.H., Noort D., van der Marel G.A., Overkleeft H.S., and Overhand M. Eur. J. Org. Chem. (2009) 4231-4241
35. Montero A., Mann E., and Herradon B. Eur. J. Org. Chem. (2004) 3063-3073
36. Montero A., Mann E., and Herradon B. Tetrahedron Lett. 46 (2005) 401-405
37. A. Montero, Ph.D. Thesis, Universidad Autónoma de Madrid, 2004.
38. Lubineau A., Canac Y., and Le Goff N. Adv. Synth. Catal. 344 (2002) 319-327
39. Krohn K., Flörke U., and Huele D. J. Carbohydr. Chem. 21 (2002) 431-443
40. The current importance of chiral halogenated chlorides can be exemplified by the recent synthesis of a chlorosulfolipid cytotoxin, see:. Nilewski C., Geisser R.W., and Carreira E.M. Nature 457 (2009) 573-577
41. In: Witczak Z.J., and Nieforth K.A. (Eds). Carbohydrate in Drug Design (2004), Marcel Dekker, NY
42. Ernst B., and Magnani J.L. Nat. Rev. Drug Disc. 8 (2009) 661-677
43. Ager D.J., Pantaleone D.P., Henderson S.A., Katritzky A.R., Prakash I., and Walters D.E. Angew. Chem., Int. Ed. 37 (1998) 1802-1817
44. Herradon B., and Valverde S. Tetrahedron: Asymmetry 5 (1994) 1479-1500
45. Herradón B., Morcuende A., and Valverde S. Synlett (1995) 455-458
46. Nishikawa T., Asai M., Ohyabu N., and Isobe M. J. Org. Chem. 63 (1998) 188-192
47. All the new compounds have been fully characterized by spectroscopic and analytical methods (see Supplementary data).
48. For selected publications on calpain and its inhibitors, see:. Goll D.E., Thompson V.F., Li H., Wei W., and Cong J. Physiol. Rev. 83 (2003) 731-801
49. Tompa P., Buzder-Lantos P., Tantos A., Farkas A., Szilagyi A., Banoczi Z., Hudecz F., and Friedrich P. J. Biol. Chem. 279 (2004) 20775-20785
50. Zatz M., and Starling A. N. Eng. J. Med. 352 (2005) 2413-2423
51. Neffe A.T., and Abell A.D. Curr. Opin. Drug Disc. Devel. 8 (2005) 684-700
52. Carragher N. Curr. Pharm. Des. 12 (2006) 615-638
53. Croall D.E., and Ersfeld K. Genome Biol. 8 (2007) 218
54. Our previous work has shown the importance of aromatic substitution on calpain inhibition, see:. Montero A., Albericio F., Royo M., and Herradon B. Org. Lett. 6 (2004) 4089-4092 and references cited therein
55. For recent examples of biologically active carbohydrates with aromatic substitution, see:. Jacobsson M., Ellervik U., Belting M., and Mani K. J. Med. Chem. 49 (2006) 1932-1936
56. Lee K.Y., Sung S.H., and Kim Y.C. J. Nat. Prod. (2006) 679-681
57. Saquib M., Gupta M.K., Sagar R., Prabhakar Y.S., Shaw A.K., Kumar R., Maulik P.R., Gaikwad A.N., Sinha S., Srivastana A.K., Chaturvedi V., Srivastana R., and Srivastana B.S. J. Med. Chem. 50 (2007) 2942-2950
58. Mitsunobu O., Yamada M., and Mukaiyama T. Bull. Chem. Soc. Jpn. 40 (1967) 935-939
59. Mitsunobu N. Synthesis (1981) 1-28
60. Wisniewski K., Koldziejczyk A.S., and Falkiewicz B. J. Peptide Sci. 4 (1998) 1-14
61. Swamy K.C.K., Kumar N.N.B., Balaraman E., and Kumar K.V.P.P. Chem. Rev. 109 (2009) 2551-2651
62. After our initial disclosure (see footnote no. 10 in Ref. 9), two articles reporting chlorinated by-products in Overman rearrangement have been published (both of them missed to cite our former article), see:. Pietruszka J., Schone N., Frey W., and Grundl L. Chem. Eur. J. 14 (2008) 5178-5197
63. Matveenko M., Willis A.C., and Banwell M.G. Aust. J. Chem. 62 (2009) 64-68
64. A minor mistake has been detected in the structures drawn in Ref. 9: the protecting group is TBDPS instead of TBDMS, we apologize for the error.
65. N2′ although the trichloroacetimidate group is essential to achieve the total selectivity (regio- and stereo-). On the other hand, DBU and trichloroacetonitrile yield a putative 2:1 DBU-Cl ate complex which is a chlorinating agent, although its structure has not been yet clarified.