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Synlett 2004(9): 1625-1627
DOI: 10.1055/s-2004-829085
DOI: 10.1055/s-2004-829085
LETTER
© Georg Thieme Verlag Stuttgart · New York
New Synthesis of a Pyrroloquinoline Skeleton, the Martinelline Core, Using a Tandem Michael-Aldol Strategy
Further Information
Received
15 April 2004
Publication Date:
29 June 2004 (online)
Publication History
Publication Date:
29 June 2004 (online)
![](https://www.thieme-connect.de/media/synlett/200409/lookinside/thumbnails/10.1055-s-2004-829085-1.jpg)
Abstract
The pyrroloquinoline moiety of Martinelline, a naturally occurring bradykinin receptor antagonist, has been synthesized from 1,2-dihydroquinoline which was prepared by using a tandem Michael-aldol reaction as a key step.
Key words
aldol reactions - Michael reactions - cyclizations - pyrroloquinoline - tandem reactions
- 1
Witherup KM.Ransom RW.Graham AC.Bernard AM.Salvature MJ.Lumma WC.Anderson PS.Pitzewberger SM.Verga SL. J. Am. Chem. Soc. 1995, 117: 6682 -
2a
He Y.Mahmud H.Wayland BR.Dias HVR.Lovely CJ. Tetrahedron Lett. 2002, 43: 1171 -
2b
Nyerges M.Fejes I.Toke L. Synthesis 2002, 1823 -
2c
Malassene R.Sanchez-Bajo L.Toupet L.Hurvois J.Moinet C. Synlett 2002, 1500 -
2d
Batey RA.Powell DA. Chem. Commun. 2001, 2362 -
2e
Mahmud H.Lovely CJ.Dias HVR. Tetrahedron 2001, 57: 4095 -
2f
Hadden M.Nieuwenhuyzen M.Potts D.Stevenson PJ.Thompson N. Tetrahedron 2001, 57: 5615 -
2g
Hadden M.Nieuwenhuyzen M.Osborne D.Stevenson PJ.Thompson N. Tetrahedron Lett. 2001, 42: 6417 -
2h
Frank KE.Aube J. J. Org. Chem. 2000, 65: 655 -
2i
Nieman JA.Ennis MD. Org. Lett. 2000, 2: 1395 -
2j
Nyerges M.Fejes I.Toke L. Tetrahedron Lett. 2000, 41: 7951 -
2k
Snider BB.Ahn Y.Foxman BM. Tetrahedron Lett. 1999, 40: 3339 -
2l
Hadden M.Stevenson PJ. Tetrahedron Lett. 1999, 40: 1215 -
2m
Batey RA.Simoncic PD.Lin D.Smyj RP.Lough AJ. Chem. Commun. 1999, 651 -
2n
Lovely CJ.Mahmud H. Tetrahedron Lett. 1999, 40: 2079 -
2o
Kim SS.Cheon HG.Kang SK.Yum EK.Choi JK. Heterocycles 1998, 48: 221 -
2p
Gurjar MK.Pal S.Rama Rao AV. Heterocycles 1997, 45: 231 -
2q
Ho TCT.Jones K. Tetrahedron 1997, 53: 8287 -
3a
Ma D.Xia C.Jiang J.Zhang J.Tang W. J. Org. Chem. 2003, 68: 442 -
3b
Xia C.Heng L.Ma D. Tetrahedron Lett. 2002, 43: 9405 -
3c
Powell DA.Batey RA. Org. Lett. 2002, 4: 2913 -
3d
Ma D.Xia C.Jiang J.Zhang J. Org. Lett. 2001, 3: 2189 -
3e
Snider BB.Ahn Y.O’Hare SM. Org. Lett. 2001, 3: 4217 - 4
Makino K.Hara O.Takiguchi Y.Katano T.Asakawa Y.Hatano K.Hamada Y. Tetrahedron Lett. 2003, 44: 8925 - 5
List B.Lerner RA.Barbas CFIII. J. Am. Chem. Soc. 2000, 122: 2395 - 6
Grundke G.Keese W.Rimpler M. Chem. Ber. 1985, 118: 4288 - 7 Compound 27: amorphous powder. IR (KBr): 3389, 2979, 1700, 1685, 1559, 1458 cm-1. 1H NMR (CDCl3, 55 °C): δ = 1.09-1.19 (m, 1 H), 1.23-1.43 (m, 22 H), 1.62-1.75 (m, 3 H), 2.37 (s, 3 H), 3.08-3.22 (m, 4 H), 4.51-4.55 (m, 2 H), 6.45 (m, 1 H), 6.54 (d, J = 2.7 Hz, 1 H), 6.73 (dd, J = 8.5, 2.4 Hz, 1 H), 7.19 (d, J = 8.1 Hz, 2 H), 7.34 (d, J = 8.5 Hz, 1 H), 7.48 (d, J = 8.1 Hz, 2 H). 13C NMR (CDCl3, 55 °C): δ = 21.4, 27.1, 28.5, 54.1, 80.0, 112.9, 114.9, 125.3, 126.9, 129.9, 130.4, 136.4, 155.7, 156.3. HRMS-FAB: m/z calcd for C31H43O7N3S: 601.2822 [M+ + 1]. Found: 601.2792 [M+ + 1]