RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2008(18): 2925-2928
DOI: 10.1055/s-2008-1067237
DOI: 10.1055/s-2008-1067237
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of a Conformationally Constrained Phenylalanine Derivative by a Strategic Combination of Ring-Closing Enyne Metathesis and Diels-Alder Reaction
Weitere Informationen
Received
29 April 2008
Publikationsdatum:
22. August 2008 (online)
Publikationsverlauf
Publikationsdatum:
22. August 2008 (online)

Abstract
An efficient route towards the synthesis of a conformationally constrained phenylalanine derivative is demonstrated using the strategic combination of ring-closing enyne metathesis and Diels-Alder reaction as key steps.
Key words
constrained amino acid - phenylalanine - ring closure - metathesis - Diels-Alder
-
1a
Pillai O.Panchagnula R. Drug Discovery Today 2001, 6: 1056 -
1b
Fletcher K. Pharm. Sci. Technol. Today 1998, 1: 49 -
1c
Cochran AG. Chem. Biol. 2000, 7: R85 -
1d
van Hest JCM.Tirrell DA. Chem. Commun. 2001, 1897 -
2a
Wang W.Cai M.Xiong C.Zhang J.Trivedi D.Hruby VJ. Tetrahedron 2002, 58: 7365 -
2b
Rajesh BM.Iqbal J. Curr. Pharm. Biotechnol. 2006, 7: 247 -
3a
Kotha S.Lahiri K. Curr. Med. Chem. 2005, 12: 849 -
3b
Liskamp RMJ. Angew. Chem., Int. Ed. Engl. 1994, 33: 305 - 4
Griffiths EC. In A Text Book of Drug Design and DevelopmentKrogsgaard L.Bundgaard P. Harwood Academic Publishers; Tokyo: 1992. p.487-528 -
5a
Gibson SE.Guillo N.Tozer MJ. Tetrahedron 1999, 55: 585 -
5b
Kazmierski W.Hruby VJ. Tetrahedron 1988, 44: 697 -
6a
Schiller PW.Nguyen TM.Weltrowska G.Wilkes BC.Marsden BJ.Lemieux C.Chung NN. Proc. Natl. Acad. Sci. U.S.A. 1992, 89: 11871 -
6b
Kazmierski WM.Yamamura HI.Hruby VJ. J. Am. Chem. Soc. 1991, 113: 2275 -
6c
Lazarus LH.Bryant SD.Cooper PS.Guerrini R.Balboni G.Salvadori S. Drug Discovery Today 1998, 3: 284 -
7a
Austin NE.Avenell KY.Boyfield I.Branch CL.Coldwell MC.Hadley MS.Jeffrey P.Johns A.Johnson CN.Nash DJ.Riley GJ.Smith SA.Stacey RC.Stemp G.Thewlis KM.Vong AKK. Bioorg. Med. Chem. Lett. 1999, 9: 179 -
7b
Chen KX.Njoroge FG.Pichardo J.Prongay A.Butkiewicz N.Yao N.Madison V.Girijavallabhan V. J. Med. Chem. 2006, 49: 567 - For selected examples:
-
8a
Manabe K.Nobutou D.Kobayashi S. Bioorg. Med. Chem. 2005, 13: 5154 -
8b
Comins DL.Thakker PM.Baevsky MF.Badawi MM. Tetrahedron 1997, 53: 16327 -
8c
Chen HG.Goel OP. Synth. Commun. 1995, 25: 49 -
8d
Jansa P.Machacek V.Bertolasi V. Heterocycles 2006, 68: 59 -
8e
Liu ZZ.Tang YF.Chen SZ. Chin. Chem. Lett. 2001, 12: 947 -
8f
Capilla AS.Romero M.Pujol MD.Caignard DH.Renard P. Tetrahedron 2001, 57: 8297 -
8g
Nicoletti M.O’Hagan D.Slawin AMZ. J. Chem. Soc., Perkin Trans. 1 2002, 116 -
8h
Mash EA.Williams LJ.Pfeiffer SS. Tetrahedron Lett. 1997, 38: 6977 -
8i
Chrzanowska M.Rozwadowska MD. Chem. Rev. 2004, 104: 3341 -
8j
Kotha S.Sreenivasachary N. J. Indian Inst. Sci. 2001, 81: 277 ; and references cited therein -
8k
Liu C.Thomas JB.Brieaddy L.Berrang B.Carroll FI. Synthesis 2008, 856 -
8l
Wohlgemuth R.Benz P. J. Chem. Technol. Biotechnol. 2007, 82: 1082 -
8m
Aubry S.Pellet-Rostaing S.Faure R.Lemaire M. J. Heterocycl. Chem. 2006, 43: 139 -
8n
Ooi T.Takeuchi M.Maruoka K. Synthesis 2001, 1716 -
8o
Shchetnikov GT.Osipov SN.Bruneau C.Dixneuf PH. Synlett 2008, 578 - For the ‘building block approach’ see:
-
9a
Kotha S. Acc. Chem. Res. 2003, 36: 342 -
9b
Corey EJ.Cheng X.-M. The Logic of Chemical Synthesis John Wiley; New York: 1989. - 10
Kotha S.Sreenivasachary N. Bioorg. Med. Chem. Lett. 2000, 10: 1413 -
11a
Kotha S.Sreenivasachary N. Chem. Commun. 2000, 503 -
11b
Kotha S.Sreenivasachary N. Eur. J. Org. Chem. 2001, 3375 -
12a
Gibson SE.Guillo N.Middleton RJ.Thuilliez A.Tozer MJ. J. Chem. Soc., Perkin Trans. 1 1997, 447 -
12b
Gibson SE.Middleton RJ. J. Chem. Soc., Chem. Commun. 1995, 1743 -
13a
Gibson SE.Guillo N.Jones JO.Buck IM.Kalindjian SB.Roberts S.Tozer MJ. Eur. J. Med. Chem. 2002, 37: 379 -
13b
Gibson SE.Guillo N.Kalindjian SB.Tozer MJ. Bioorg. Med. Chem. Lett. 1997, 7: 1289 - For selected reviews on enyne metathesis, see:
-
14a
Hansen EC.Lee D. Acc. Chem. Res. 2006, 39: 509 -
14b
Maifeld SV.Lee D. Chem. Eur. J. 2005, 11: 6118 -
14c
Diver ST.Giessert AJ. Chem. Rev. 2004, 104: 1317 -
14d
Poulsen CS.Madsen R. Synthesis 2003, 1 - 15
Fringuelli F.Taticchi A. The Diels-Alder Reaction: Selected Practical Methods John Wiley & Sons; Chichester: 2002. -
16a
Schwab P.Grubbs RH.Ziller JW. J. Am. Chem. Soc. 1996, 118: 100 -
16b
Schwab P.France MB.Ziller JW.Grubbs RH. Angew. Chem., Int. Ed. Engl. 1995, 34: 2039 -
16c
Wu Z.Nguyen ST.Grubbs RH.Ziller JW. J. Am. Chem. Soc. 1995, 117: 5503 -
16d
Scholl M.Ding S.Lee CW.Grubbs RH. Org. Lett. 1999, 1: 953 - 17
Brahmachary E. PhD Thesis IIT-Bombay; India: 2000.