Stereoselective Synthesis of Aza- and Diazabicyclo[X.Y.0]alkane Dipeptide Mimetics

Wolfgang Maison; Alexander H. G. P. Prenzel

doi:10.1055/s-2005-865295

REVIEW

Stereoselective Synthesis of Aza- and Diazabicyclo[X.Y.0]alkane Dipeptide Mimetics

Wolfgang Maison*, Alexander H. G. P. Prenzel
Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany
Fax: +49(40)428382495; e-Mail: maison@chemie.uni-hamburg.de;

Abstract

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Abstract

This review focuses on recent synthetic developments for the stereoselective preparation of aza- and diazabicyclo[X.Y.0]alkane dipeptide mimetics of the general structures 1-3. Different synthetic strategies are compared with respect to stereoselectivity as well as flexibility regarding ring sizes, stereochemistry and introduction of side-chains.

1 Introduction
2 Azabicycloalkanes
2.1 Lactam Formation
2.2 Radical Cyclization
2.3 Dieckmann Cyclization
2.4 Iodo- and Selenocyclization
2.5 Ring-Closing Metathesis
2.6 N-Acyliminium Cyclization
3 Diazabicycloalkanes
3.1 Lactam Formation
3.2 Ring-Closing Metathesis
3.3 Intramolecular Reductive Amination
3.4 N-Acyliminium Cyclization
3.5 Tandem Cyclization
4 Summary

Key words

peptides - bicyclic compounds - lactams - stereoselective synthesis - heterocycles

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References

1 Gillespie P. Cicariello J. Olson GL. Biopolymers 1997, 43: 191

2 Müller CW. Curr. Opin. Struct. Biol. 2001, 11: 26

3 Rose GD. Gierasch LM. Smith JA. Adv. Protein Chem. 1985, 37: 1

4a Bode W. Huber R. Eur. J. Biochem. 1992, 204: 433

4b Wu TP. Yee V. Tulinsky A. Chrusciel RA. Nakanishi H. Shen R. Priebe C. Kahn M. Protein Eng. 1993, 6: 471

5 Pascal SM. Singer AU. Gish G. Yamazaki T. Shoelson SE. Pawson T. Kay LE. Forman-Kay JD. Cell 1994, 77: 461

6 Brown JH. Jardetzky TS. Gorga JC. Stern LJ. Urban RG. Strominger JL. Wiley DC. Nature 1993, 364: 33

7a Gante J. Angew. Chem., Int. Ed. Engl. 1994, 33: 1699 ; Angew. Chem. 1994, 106, 1780

7b Giannis A. Kolter T. Angew. Chem., Int. Ed. Engl. 1993, 32: 1244 ; Angew. Chem. 1993, 105, 1303

For reviews on cyclic peptides as turn mimetics, see:

8a Souers AJ. Ellman JA. Tetrahedron 2001, 57: 7431

8b Burgess K. Acc. Chem. Res. 2001, 34: 826

9 Haubner R. Finsinger D. Kessler H. Angew. Chem., Int. Ed. Engl. 1997, 36: 1374 ; Angew. Chem. 1997, 109, 1440

10a Otaka A. Katagiri F. Kinoshita T. Odagaki Y. Oishi S. Tamamura H. Hamanaka N. Fujii N. J. Org. Chem. 2002, 67: 6152

10b Hruby VJ. Balse PM. Curr. Med. Chem. 2000, 7: 945

11 Hruby VJ. Li G. Haskell-Luevano C. Shenderovich M. Biopolymers 1997, 43: 219

12 Kim HO. Kahn M. Comb. Chem. High Throughput Screening 2000, 3: 167

13 Halab L. Gosselin F. Lubell WD. Biopolymers 2000, 55: 101

14 Eguchi M. McMillan M. Nguyen C. Teo J.-l. Chi EY. Henderson WR. Kahn M. Comb. Chem. High Throughput Screening 2003, 6: 611

15a Maison W. Grohs DC. Prenzel AHGP. Eur. J. Org. Chem. 2004, 1527

15b Belvisi L. Bernardi A. Checchia A. Manzoni L. Potenza D. Scolastico C. Castorina M. Cupelli A. Giannini G. Carminati P. Pisano C. Org. Lett. 2001, 3: 1001

15c Belvisi L. Caporale A. Colombo M. Manzoni L. Potenza D. Scolastico C. Castorina M. Cati M. Giannini G. Pisano C. Helv. Chim. Acta 2002, 85: 4353

16 Hanessian S. McNaughton-Smith G. Lombart H.-G. Lubell WD. Tetrahedron 1997, 53: 12789

17 Suat Kee K. Jois SDS. Curr. Pharm. Des. 2003, 9: 1209

For reviews see:

18a Michael JP. Nat. Prod. Rep. 2004, 21: 625 ; and previous articles of this series

18b Yoda H. Curr. Org. Chem. 2002, 6: 223

18c Felpin F.-X. Lebreton J. Eur. J. Org. Chem. 2003, 3693

19a Hanessian S. Ronan B. Laoui A. Bioorg. Med. Chem. Lett. 1994, 4: 1397

19b Hanessian S. McNaughton-Smith G. Bioorg. Med. Chem. Lett. 1996, 6: 1567

20 Katoh T. Nagata Y. Kobayashi Y. Arai K. Minami J. Terashima S. Tetrahedron Lett. 1993, 34: 5743

21a Hanessian S. Balaux E. Musil D. Olsson L.-L. Nilsson I. Bioorg. Med. Chem. Lett. 2000, 10: 243

21b Hanessian S. Therrien E. Granberg K. Nilsson I. Bioorg. Med. Chem. Lett. 2002, 12: 2907

22 Vishwakarma LC. Stringer OD. Davis F. Org. Synth. 1988, 66: 203

23 Hanessian S. Reinhold U. Gentile G. Angew. Chem., Int. Ed. Engl. 1997, 36: 1881 ; Angew. Chem. 1997, 109, 1953

24 Hanessian S. Buckle R. Bayrakdarian M. J. Org. Chem. 2002, 67: 3387

25 Mulzer J. Schülzchen F. Bats J.-W. Tetrahedron 2000, 56: 4289

26 Bravin FM. Busnelli G. Colombo M. Gatti F. Manzoni L. Scolastico C. Synthesis 2004, 353

27 Wang W. Yang J. Ying J. Xiong C. Zhang J. Cai C. Hruby VJ. J. Org. Chem. 2002, 67: 6353

28 Angiolini M. Araneo S. Belvisi L. Cesarotti E. Checchia A. Crippa L. Manzoni L. Scolastico C. Eur. J. Org. Chem. 2000, 2571

29a Belvisi L. Bernardi A. Manzoni L. Potenza D. Scolastico C. Eur. J. Org. Chem. 2000, 2563

29b Manzoni L. Colombo M. May E. Scolastico C. Tetrahedron 2001, 57: 249

29c Artale E. Banfi G. Belvisi L. Colombo L. Colombo M. Manzoni L. Scolastico C. Tetrahedron 2003, 59: 6241

29d Belvisi L. Colombo L. Manzoni L. Potenza D. Scolastico C. Synlett 2004, 1449

30 Manzoni L. Belvisi L. Colombo M. Di Carlo E. Forni A. Scolastico C. Tetrahedron Lett. 2004, 45: 6311

31 Zhang J. Xiong C. Ying J. Wang W. Hruby VJ. Org. Lett. 2003, 5: 3115

32 Coleman RS. Carpenter AJ. J. Org. Chem. 1993, 58: 4452

33 Zhang J. Xiong C. Wang W. Ying J. Hruby VJ. Org. Lett. 2002, 4: 4029

34a Mueller R. Revesz L. Tetrahedron Lett. 1994, 35: 4091

34b Lombart H.-G. Lubell WD. J. Org. Chem. 1994, 59: 6147

35 Schoellkopf U. Top. Curr. Chem. 1983, 109: 65

36 Lombart H.-G. Lubell WD. J. Org. Chem. 1996, 61: 9437

37 Kim H.-O. Kahn M. Tetrahedron Lett. 1997, 38: 6483

38 Feng Z. Lubell WD. J. Org. Chem. 2001, 66: 1181

39 Polyak F. Lubell WD. J. Org. Chem. 2001, 66: 1171

40 Polyak F. Lubell WD. J. Org. Chem. 1998, 63: 5937

41 Dietrich E. Lubell WD. J. Org. Chem. 2003, 68: 6988

42 Gosselin F. Lubell WD. J. Org. Chem. 1998, 63: 7463

43 Gosselin F. Lubell WD. J. Org. Chem. 2000, 65: 2163

44 Cluzeau J. Lubell WD. J. Org. Chem. 2004, 69: 1504

45 Wang W. Xiong C. Hruby VJ. Tetrahedron Lett. 2001, 42: 3159

46 Lamazzi C. Carbonnel S. Calinaud P. Troin Y. Heterocycles 2003, 60: 1447

47 Shimizu M. Nemoto H. Kakuda H. Takahata H. Heterocycles 2003, 59: 245

48 Millet R. Domarkas J. Rombaux P. Rigo B. Houssin R. Hénichart J.-P. Tetrahedron Lett. 2002, 43: 5087

49 Tong Y. Olczak J. Zabrocki J. Gershengorn MC. Marshall GR. Moeller KD. Tetrahedron 2000, 56: 9791

50 Cordero FM. Valenza S. Machetti F. Brandi A. Chem. Commun. 2001, 1590

51 Colombo L. Di Giacomo M. Papeo G. Carugo O. Scolastico C. Manzoni L. Tetrahedron Lett. 1994, 35: 4031

52 Chiesa MV. Mazoni L. Scolastico C. Synlett 1996, 441

53 Colombo L. Di Giacomo M. Brusotti G. Sardone N. Angiolini M. Belvisi L. Maffioli S. Manzoni L. Scolastico C. Tetrahedron 1998, 54: 5325

54 Colombo L. Di Giacomo M. Scolastico C. Manzoni L. Belvisi L. Molteni V. Tetrahedron Lett. 1995, 36: 625

55 Manzoni L. Belvisi L. Scolastico C. Synlett 2000, 1287

56 Lindemann U. Reck G. Wulff-Molder D. Wessig P. Tetrahedron: Asymmetry 1998, 9: 4459

57 Wessig P. Tetrahedron Lett. 1999, 40: 5987

58 Hanessian S. Sailes H. Munro A. Therrien E. J. Org. Chem. 2003, 68: 7219

59 Hanessian S. Papeo G. Fettis K. Therrien E. Viet MTP. J. Org. Chem. 2004, 69: 4891

60 Westermann B. Gedrath I. Synlett 1996, 665

61 Westermann B. Diedrichs N. Krelaus R. Walter A. Gedrath I. Tetrahedron Lett. 2004, 45: 5983

62 Elliot CE. Miller DO. Burnell DJ. J. Chem. Soc., Perkin Trans. 1 2002, 217

For reviews, see:

63a Fürstner A. Angew. Chem. Int. Ed. 2000, 17: 3012 ; Angew. Chem. 2000, 112, 3140

63b Wright DL. Curr. Org. Chem. 1999, 3: 211

64 Overkleeft HS. Pandit UK. Tetrahedron Lett. 1996, 37: 547

For reviews, see:

65a Vernall AJ. Abell AD. Aldrichimica Acta 2003, 36: 93

65b Arjona O. Csaky AG. Plumet J. Eur. J. Org. Chem. 2003, 611

65c Phillips AJ. Abell AD. Aldrichimica Acta 1999, 32: 75

66 Miller SJ. Grubbs RH. J. Am. Chem. Soc. 1995, 117: 5855

67 Beal LM. Moeller KD. Tetrahedron Lett. 1998, 39: 4639

68 Grossmith CE. Senia F. Wagner J. Synlett 1999, 1660

69 For a review of anodic electrochemistry in organic synthesis see: Moeller KD. Tetrahedron 2000, 56: 9527

70 Beal LM. Liu B. Chu W. Moeller KD. Tetrahedron 2000, 56: 10113

71 Lim SH. Ma S. Beak P. J. Org. Chem. 2001, 66: 9056

72 Manzoni L. Colombo M. Scolastico C. Tetrahedron Lett. 2004, 45: 2623

73 Harris PWR. Brimble MA. Gluckman PD. Org. Lett. 2003, 5: 1847

74 Krelaus R. Westermann B. Tetrahedron Lett. 2004, 45: 5987

75 Hoffmann T. Lanig H. Waibel R. Gmeiner P. Angew. Chem. Int. Ed. 2001, 40: 3361 ; Angew. Chem. 2001, 113, 3465

76 Seebach D. Boes M. Naef R. Schweizer WB. J. Am. Chem. Soc. 1983, 105: 5390

77 Wang H. Germanas JP. Synlett 1999, 33

78a Moeller KD. Hanau CE. d’Avignon A. Tetrahedron Lett. 1994, 35: 825

78b In a first paper, the structure of 121c was incorrectly assigned to be the corresponding 7,5-fused analog: Moeller KD. Rothfus SL. Tetrahedron Lett. 1992, 33: 2913

79 Li W. Hanau CE. d’Avignon A. Moeller KD. J. Org. Chem. 1995, 60: 8155

80 Li W. Moeller KD. J. Am. Chem. Soc. 1996, 118: 10106

81 Chu W. Moeller KD. Tetrahedron Lett. 1999, 40: 7939

82 Robl JA. Tetrahedron Lett. 1994, 35: 393

83 Yoshida J. Top. Curr. Chem. 1994, 170: 39

84 Sun H. Moeller KD. Org. Lett. 2002, 4: 1547

85 For a review on the use of pyroglutamates in asymmetric synthesis, see: Najera C. Yus M. Tetrahedron: Asymmetry 1999, 10: 2245

86 St. Denis Y. Augelli-Szafran CE. Bachand B. Berryman KA. DiMaio J. Doherty AM. Edmunds JJ. Leblond L. Levesque S. Narasimhan LS. Penvose-Yi JR. Rubin JR. Tarazi M. Winocour PD. Siddiqui MA. Bioorg. Med. Chem. Lett. 1998, 8: 3193

87a Thaning M. Wistrand LG. Acta Chem. Scand. 1992, 46: 194

87b Ludwig C. Wistrand LG. Acta Chem. Scand. 1994, 48: 367

88 McClure KF. Renold P. Kemp DS. J. Org. Chem. 1995, 60: 454

89 Plummer JS. Berryman KA. Cai C. Cody WL. DiMaio J. Doherty AM. Edmunds JJ. He JX. Holland DR. Levesque S. Kent DR. Narasimhan LS. Rubin JR. Rapundalo ST. Siddiqui MA. Susser AJ. St. Denis Y. Winocourt PD. Bioorg. Med. Chem. Lett. 1998, 8: 3409

90 Chan MF. Raju BG. Kois A. Varughese JI. Varughese KI. Balaji VN. Heterocycles 1999, 51: 5

91 Cignarella G. Nathanson G. J. Org. Chem. 1961, 26: 1500

92 Fobian YM. d’Avignon DA. Moeller KD. Bioorg. Med. Chem. Lett. 1996, 6: 315

93 Carpino LA. Beyermann M. Wenschuh H. Bienert M. Acc. Chem. Res. 1996, 29: 268

94 Duan S. Moeller KD. Tetrahedron 2001, 57: 6407

95 Tong Y. Fobian YM. Wu M. Boyd ND. Moeller KD. J. Org. Chem. 2000, 65: 2484

96a This strategy has first been used by Steglich and coworkers to incorporate 3,5-substituted proline derivatives into peptides: Jäger M. Polborn K. Steglich W. Tetrahedron Lett. 1995, 36: 861

96b Maison W. Adiwidjaja G. Tetrahedron Lett. 2002, 43: 5957

97 Maison W. Küntzer D. Grohs D. Synlett 2002, 1795

98 Abraham H. Stella L. Tetrahedron 1992, 48: 9707

99 Maison W. Frangioni JV. Angew. Chem. Int. Ed. 2003, 42: 4726 ; Angew. Chem. 2003, 115, 4874

100 For in situ oxidative diol cleavage-Wittig processes, see: Outram HS. Raw SA. Taylor RJK. Tetrahedron Lett. 2002, 43: 6185