Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2005(7): 1031-1048
DOI: 10.1055/s-2005-865295
DOI: 10.1055/s-2005-865295
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Stereoselective Synthesis of Aza- and Diazabicyclo[X.Y.0]alkane Dipeptide Mimetics
Further Information
Received
10 January 2005
Publication Date:
23 March 2005 (online)
Publication History
Publication Date:
23 March 2005 (online)
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
- 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