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 2007(19): 3061-3067
DOI: 10.1055/s-2007-983901
DOI: 10.1055/s-2007-983901
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of s-Indacene Derivatives by Double Robinson-Type Cyclopentene Annulation
Further Information
Received
4 May 2007
Publication Date:
11 September 2007 (online)
Publication History
Publication Date:
11 September 2007 (online)
![](https://www.thieme-connect.de/media/synthesis/200719/lookinside/thumbnails/10.1055-s-2007-983901-1.jpg)
Abstract
Michael reactions of 2,5-dioxocyclohexane-1,4-dicarboxylates with methyl vinyl ketone yield bis-adducts that can be further cyclized in a Robinson-type annulation to give s-indacene derivatives as single diastereomers. The carboxylate functions of this scaffold can be deprotected and subsequently decarboxylated to yield tricyclic products with a central aromatic ring.
Key words
annulation - indacene - cyclopentene - conjugate addition - aldol reaction
- 1
Modern Aldol Reactions
Mahrwald R. Wiley-VCH; Weinheim: 2004. - 2
Christoffers J. In Encyclopedia of Catalysis Vol. 5:Horvath I. Wiley; New York: 2003. p.99 -
3a
Rapson WS.Robinson R. J. Chem. Soc. 1935, 1285 - Reviews:
-
3b
Gawley RE. Synthesis 1976, 777 -
3c
Jung ME. Tetrahedron 1976, 32: 3 - Recent examples:
-
4a
Kraft P.Weymuth C.Nussbaumer C. Eur. J. Org. Chem. 2006, 1403 -
4b
Röttger S.Waldmann H. Eur. J. Org. Chem. 2006, 2093 -
4c
Payette JN.Honda T.Yoshizawa H.Favaloro FG.Gribble GW. J. Org. Chem. 2006, 71: 416 -
4d
Gan Y.Spencer TA. J. Org. Chem. 2006, 71: 5870 -
5a
Kreidler B.Baro A.Christoffers J. Eur. J. Org. Chem. 2005, 5339 -
5b
Kreidler B.Baro A.Frey W.Christoffers J. Chem. Eur. J. 2005, 11: 2660 -
5c
Kreidler B.Baro A.Christoffers J. Synlett 2005, 465 - Review:
-
5d
Christoffers J. Chem. Eur. J. 2003, 9: 4862 -
6a
Christoffers J. Synlett 2006, 318 -
6b
Christoffers J.Scharl H.Frey W.Baro A. Eur. J. Org. Chem. 2004, 2701 -
6c
Christoffers J.Scharl H.Frey W.Baro A. Org. Lett. 2004, 6: 1171 -
6d
Christoffers J.Scharl H. Eur. J. Org. Chem. 2002, 1505 - 7
Christoffers J.Zhang Y.Frey W.Fischer P. Synlett 2006, 624 - 8
Buchanan GL.Kennedy WB.Lawson AM. J. Chem. Soc., Perkin Trans. 1 1977, 32 -
9a
García Cuesta I.Coriani S.Lazzeretti P.Sánchez de Merás AMJ. ChemPhysChem 2006, 7: 240 -
9b
Güell M.Matito E.Luis JM.Poater J.Sola M. J. Phys. Chem. A 2006, 110: 11569 -
10a
Dahrouch M.Burgos F.Castel A.Chavez I.Gornitzka H.Manriquez JM.Riviere P.Riviere-Baudet M.Alvarez J.Onyszchuk M. Appl. Organomet. Chem. 2007, 21: 31 -
10b
Lian J.-J.Lin C.-C.Chang H.-K.Chen P.-C.Liu R.-S. J. Am. Chem. Soc. 2006, 128: 9661 -
10c
Dahrouch MR.Jara P.Mendez L.Portilla Y.Abril D.Alfonso G.Chavez I.Manriquez JM. Organometallics 2001, 20: 5591 -
10d
Hafner K.Stowasser B.Krimmer H.-P.Fischer S.Böhm MC.Lindner HJ. Angew. Chem., Int. Ed. Engl. 1986, 25: 630 ; Angew. Chem. 1986, 98, 646 -
10e
Birladeanu L.Chamot E.Fristad WE.Paquette LA.Winstein S. J. Org. Chem. 1977, 42: 3260 -
10f
LeGoff E.LaCount RB. Tetrahedron Lett. 1964, 5: 1161 -
11a
Hudlicky T.Fleming A.Radesca L. J. Am. Chem. Soc. 1989, 111: 6691 -
11b
Woodward RB.Hoye TR. J. Am. Chem. Soc. 1977, 99: 8007 -
12a
Esponda E.Adams C.Burgos F.Chavez I.Manriquez JM.Delpech F.Castel A.Gornitzka H.Riviere-Baudet M.Riviere P. J. Organomet. Chem. 2006, 691: 3011 -
12b
Roussel P.Cary DR.Barlow S.Green JC.Varret F.O’Hare D. Organometallics 2000, 19: 1071 -
12c
Bell WL.Curtis CJ.Eigenbrot CW.Pierpont CP.Robbins JL.Smart JC. Organometallics 1987, 6: 266 -
13a
Chen HZ.Jin YD.Xu RS.Peng BX.Desseyn H.Janssens J.Heremans P.Borghs G.Geise HJ. Synth. Met. 2003, 139: 529 -
13b
Halterman RL.Jan S.-T.Abdulwali AH.Standlee DJ. Tetrahedron 1997, 53: 11277 -
14a
Bauer M.Kauf T.Christoffers J.Bertagnolli H. Phys. Chem. Chem. Phys. 2005, 7: 2664 -
14b
Pelzer S.Kauf T.van Wüllen C.Christoffers J. J. Organomet. Chem. 2003, 684: 308 - Review:
-
14c
Christoffers J. Synlett 2001, 723 - 15
Christoffers J.Oertling H.Önal N. J. Prakt. Chem. 2000, 342: 546 - 16
Christoffers J.Schuster K. Chirality 2003, 15: 777 - 17
Christoffers J.Mann A. Eur. J. Org. Chem. 2000, 1977 - 18
Tsuji J.Nisar M.Shimizu I. J. Org. Chem. 1985, 50: 3416 - 19
Liebermann H. Justus Liebigs Ann. Chem. 1914, 404: 272 - 20
Moore JA. Org. Prep. Proced. Int. 1972, 4: 31 -
21a
Kan RO. J. Am. Chem. Soc. 1964, 86: 5180 -
21b
Bischoff CA.von Hedenström A. Chem. Ber. 1902, 35: 4073 - 22
Sinnreich J.Batzer H. Helv. Chim. Acta 1979, 62: 1682 - 23
Akutsu M. inventors; JP 61011290. ; Chem. Abstr. 1986, 105, 33055 - 24
Takahashi K.Shibagaki M.Matsushita H. Bull. Chem. Soc. Jpn. 1989, 62: 2353