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Synthesis 2009(2): 243-250
DOI: 10.1055/s-0028-1083298
DOI: 10.1055/s-0028-1083298
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Regioselective Synthesis of Functionalized Biaryls Based on the First [3+3] Cyclocondensations of 4-Aryl-1,3-bis(trimethylsilyloxy)buta-1,3-dienes
Further Information
Received
6 August 2008
Publication Date:
19 December 2008 (online)
Publication History
Publication Date:
19 December 2008 (online)
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Abstract
Sterically encumbered biaryls were regioselectively prepared by formal [3+3] cyclocondensations of novel 4-aryl-1,3-bis(trimethylsilyloxy)-1,3-dienes.
Key words
cyclizations - salicylates - biaryls - silyl enol ethers
- Cynandiones A-C:
-
1a
Lin Y.-L.Wu Y.-M.Kuo Y.-H. Phytochemistry 1997, 45: 1057 -
1b
Huang P.-L.Won S.-J.Day S.-H.Lin C.-N. Helv. Chim. Acta 1999, 82: 1716 -
1c
Lin Y.-L.Lin T.-C.Kuo Y.-H. J. Nat. Prod. 1997, 60: 368 -
1d
Buchanan MS.Gill M.Yu J. J. Chem. Soc., Perkin Trans. 1 1997, 919 - Knipholone:
-
2a 6′-O-Methylknipholone:
van Staden LF.Drewes SE. Phytochemistry 1994, 35: 685 -
2b (+)-Asphodelin:
Bezabih M.Motlhagodi S.Abegaz BM. Phytochemistry 1997, 46: 1063 -
2c
Adinolfi M.Lanzetta R.Marciano CE.Parrilli M.De Giulio A. Tetrahedron 1991, 47: 4435 - Secalonic acid A:
-
3a Globulixanthone E:
Pettit GR.Meng Y.Herald DL.Graham KAN.Pettit RK.Doubek DL. J. Nat. Prod. 2003, 66: 1065 -
3b
Nkengfack AE.Mkounga P.Meyer M.Fomum ZT.Bodo B. Phytochemistry 2002, 61: 181 - 2,3-Dihydroamentoflavone:
-
4a Bartramiaflavone:
Das B.Mahender G.Rao YK.Prabhakar A.Jagadeesh B. Chem. Pharm. Bull. 2005, 53: 135 -
4b Robustaflavone:
Basile A.Sorbo S.Lopez-Saez JA.Cobianchi RC. Phytochemistry 2003, 62: 1145 -
4c Dichamanetin:
Chen J.-J.Duh C.-Y.Chen J.-F. Planta Med. 2005, 71: 659 -
4d
Anam EM.Ekpa OD.Gariboldi PV.Morah FNI.Dosunmu MI. Indian J. Chem., Sect. B 1993, 32: 1051 -
4e
Dasgupta B.Burke B. A.Stuart K. L. Phytochemistry 1981, 20: 153 -
4f
Zeng G.-Z.Tan N.-H.Hao X.-J.Mu Q.-Z.Li R.-T. Bioorg. Med. Chem. Lett. 2006, 16: 6178 -
4g
Zeng G.-Z.Pan X.-L.Tan N.-H.Xiong J.Zhang Y.-M. Eur. J. Med. Chem. 2006, 41: 1247 - 5
Anastatin A.Yoshikawa M.Xu F.Morikawa T.Ninomiya K.Matsuda H. Bioorg. Med. Chem. Lett. 2003, 13: 1045 - 6
Metal-Catalyzed
Cross-Coupling Reactions
de Meijere A.Diederich F. Wiley-VCH; Weinheim: 2004. - 7 For a review of stereoselective syntheses
of functionalized biaryls, see:
Bringmann G.Mortimer AJM.Keller PA.Gresser MJ.Garner J.Breuning M. Angew. Chem. Int. Ed. 2005, 44: 5384 -
8a
Chan T.-H.Brownbridge P. J. Am. Chem. Soc. 1980, 102: 3534 -
8b
Brownbridge P.Chan T.-H.Brook MA.Kang GJ. Can. J. Chem. 1983, 61: 688 - 9 Review of [3+3] cyclizations:
Feist H.Langer P. Synthesis 2007, 327 - 10 Review of 1,3-bis(trimethylsilyloxy)-1,3-dienes:
Langer P. Synthesis 2002, 441 - 11
Sher M.Ahmed Z.Rashid MA.Fischer C.Langer P. J. Org. Chem. 2007, 72: 6284 - 13
Bose G.Nguyen VTH.Ullah E.Lahiri S.Görls H.Langer P. J. Org. Chem. 2004, 69: 9128 - 14
Langer P.Appel B. Tetrahedron Lett. 2003, 44: 5133 - 15
Appel B.Rotzoll S.Reinke H.Langer P. Eur. J. Org. Chem. 2006, 3638
References
CCDC-696027 (5b) and CCDC-665870 (5c) contain all crystallographic details of this publication which are available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: +44 (1223)336033, or deposit@ccdc.cam.ac.uk.