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Synthesis 2002(13): 1823-1828
DOI: 10.1055/s-2002-33922
DOI: 10.1055/s-2002-33922
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Convenient Synthesis of the Pyrrolo[3,2-c]quinoline Core of Martinelline Alkaloids
Further Information
Received
17 May 2002
Publication Date:
09 September 2002 (online)
Publication History
Publication Date:
09 September 2002 (online)
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Abstract
The tricyclic core of the martinellines has been synthesised stereoselectively in two steps, using 1,3-dipolar cycloaddition of azomethine ylides as a key step.
Key words
amino acids and derivatives - cycloadditions - pyrrolidines - quinolines
- 1
Witherup K.Ranson RW.Graham AC.Barnard AM.Salvatore MJ.Limma WC.Anderson PS.Pitzenberger SM.Varga SL. J. Am. Chem. Soc. 1995, 117: 6682 -
2a
Brown TH.Ife RJ.Keeling DJ.Laing SM.Shiona M.Leach CA. J. Med. Chem. 1990, 33: 527 -
2b
Badawey E.-SAM.Kappe T. Eur. J. Med. Chem. Chim. Ther. 1997, 32: 815 -
2c
Leach CA.Brown TH.Ife RJ.Keeling DJ.Laing SM.Parsons ME.Price CA.Wiggal KJ. J. Med. Chem. 1992, 35: 1845 - 3
Heidempergher F.Pevarello P.Pillan A.Pinciroli V.Della Torre A.Speciale C.Marconi M.Cini M.Toma S.Greco F.Varasi M. Farmaco 1999, 54: 152 -
4a
He Y.Mahmud H.Wayland BR.Dias HVR.Lovely CJ. Tetrahedron Lett. 2002, 43: 1171 -
4b
Ruano JLG.Tito A.Peromingo MT. J. Org. Chem. 2002, 67: 981 -
4c
Batey RA.Powell DA. Chem. Commun. 2001, 2362 -
4d
Browning RG.Mahmud H.Badarinarayana V.Lovely CJ. Tetrahedron Lett. 2001, 42: 7155 -
4e
Hadden M.Nieuwenhuyzen M.Osborne D.Stevenson PJ.Thompson N. Tetrahedron Lett. 2001, 42: 6417 -
4f
Hadden M.Nieuwenhuyzen M.Potts D.Stevenson PJ.Thompson N. Tetrahedron 2001, 57: 5615 -
4g
Mahmud H.Lovely CJ.Dias HVR. Tetrahedron 2001, 57: 4095 -
4h
Snider BB.O’Hare SM. Tetrahedron Lett. 2001, 42: 2455 -
4i
Nieman JA.Ennis MD. Org. Lett. 2000, 2: 1395 -
4j
Frank EC.Aubé J. J. Org. Chem. 2000, 65: 655 -
4k
Hadden M.Stevenson PJ. Tetrahedron Lett. 1999, 40: 1215 -
4l
Batey RA.Simoncic PD.Lin D.Smyj RP.Lough A. Chem. Commun. 1999, 651 -
4m
Snyder BB.Ahn Y.Foxman BM. Tetrahedron Lett. 1999, 40: 3339 -
4n
Lovely CJ.Mahmud H. Tetrahedron Lett. 1999, 40: 2079 -
4o
Kang SK.Park SS.Kim SS.Choi J.-K.Yum EK. Tetrahedron Lett. 1999, 40: 4379 -
4p
Gujar MK.Pal S.Rao AVR. Heterocycles 1997, 45: 231 -
4q
Ho TCT.Jones K. Tetrahedron 1997, 53: 8287 -
4r
Martin SF.Cheavens TH. Tetrahedron Lett. 1989, 30: 7017 -
5a
Ma D.Xia C.Jiang J.Zhang J. Org. Lett. 2001, 3: 2189 -
5b
Snider BB.Ahn Y.O" Hare SM. Org. Lett. 2001, 3: 4217 - 6 A part of these results has been
reported as a preliminary communication:
Fejes I.Nyerges M.Tõke L. Tetrahedron Lett. 2000, 40: 7951 - 7
Nyerges M.Fejes I.Virányi A.Groundwater PW.Tõke L. Tetrahedron Lett. 2001, 42: 5081 -
8a
Tsuge O.Kanemasa S. Adv. Heterocycl. Chem. 1989, 45: 232 -
8b
Grigg R.Sridharan V. In Advances in Cycloaddition Vol. 3:Curran DP. JAI Press; New York: 1993. p.161 -
8c
Nyerges M.Rudas M.Tóth G.Herényi B.Kádas I.Bitter I.T L. Tetrahedron 1995, 51: 13321ke -
8d
Fejes I.Nyerges M.Tõke L.Pak CS. Tetrahedron 2000, 56: 639 - 9 The preparation of the 3-(3-quinolyl)alanine
known from the literature is a multistep, low-yield process:
Dyer E.Yokoyama W. J. Org. Chem. 1961, 26: 2124 - 10 A similar reaction has been described
with the methyl ester of 10:
Hadden M.Stevenson PJ. J. Chem. Res., Synop. 1998, 796 ; this fact unfortunately was overlooked before C. J. Lovely’s personal reflection on our preliminary communication