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Synthesis 2009(19): 3285-3292
DOI: 10.1055/s-0029-1216953
DOI: 10.1055/s-0029-1216953
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkTotal Synthesis of (+)-Dodoneine and Its 6-Epimer
Weitere Informationen
Received
20 March 2009
Publikationsdatum:
21. August 2009 (online)
Publikationsverlauf
Publikationsdatum:
21. August 2009 (online)
Abstract
The total synthesis of dodoneine and its 6-epimer is described, using HKR of epoxide and reduction with SmI2 reactions as key steps, respectively.
Key words
dodoneine - epidodoneine - trimethylsulfonium iodide - HKR - SmI2 - RCM
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Ouedragogo M.Carreyre H.Vandebrouck C.Bescond J.Raymond G.Guissou I.-P.Cognard C.Becq F.Potreau D.Cousson A.Marrot J.Coustard J.-M. J. Nat. Prod. 2007, 70: 2006 - 2a
Robert R.Thoreau V.Norez C.Cantereau A.Mettey Y.Rogier C.Becq F. J. Biol. Chem. 2004, 279: 21160 - 2b
Vandebrouck C.Melin P.Norez C.Robert R.Guibert C.Mettey Y.Becq F. Respir. Res. 2006, 7: 113 - 3a
Bercedo PA.Falomir E.Murga J.Carda M.Marco JA. Eur. J. Org. Chem. 2008, 4015 - 3b
Srihari P.Rajendar G.Rao RS.Yadav JS. Tetrahedron Lett. 2008, 49: 5590 - 3c
Dittoo A.Bellosta V.Cooy J. Synlett 2008, 2459 - 4a
Sabitha G.Sudhakar K.Reddy NM.Rajkumar M.Yadav JS. Tetrahedron Lett. 2005, 46: 6567 - 4b
Sabitha G.Narjis F.Swapna R.Yadav JS. Synthesis 2006, 2879 - 4c
Sabitha G.Reddy EV.Yadagiri K.Yadav JS. Synthesis 2006, 3270 - 4d
Sabitha G.Sudhakar K.Yadav JS. Tetrahedron Lett. 2006, 47: 8599 - 4e
Sabitha G.Bhaskar V.Yadav JS. Tetrahedron Lett. 2006, 47: 8179 - 4f
Sabitha G.Swapna R.Reddy EV.Yadav JS. Synthesis 2006, 4242 - 4g
Sabitha G.Bhikshapathi M.Yadav JS. Synth. Commun. 2007, 37: 561 - 4h
Sabitha G.Gopal P.Yadav JS. Synth. Commun. 2007, 37: 1495 - 4i
Sabitha G.Yadagiri K.Yadav JS. Tetrahedron Lett. 2007, 48: 1651 - 4j
Sabitha G.Gopal P.Reddy CN.Yadav JS. Tetrahedron: Asymmetry 2009, 20: 184 - 5
Lescure P.Huet F. Synthesis 1987, 404 - 6a
Schaus SE.Brandes BD.Larrow JF.Tokunaga M.Hansen KB.Gould AE.Furrow ME.Jacobsen EN. J. Am. Chem. Soc. 2002, 124: 1307 - 6b
Louis JT.Nelson WL. J. Org. Chem. 1987, 52: 1309 - 7
Rychnovsky SD.Rogers BN.Richardson RI. Acc. Chem. Res. 1998, 31: 9 - 8a
Fürstner A. Angew. Chem. Int. Ed. 2000, 39: 3012 - 8b
Tanaka TM.Grubbs RH. Acc. Chem. Res. 2001, 34: 18 - 8c
Grubbs RH. Tetrahedron 2004, 44: 2449 - 8d
Grubbs RH. Tetrahedron 2004, 60: 7117 - 8e
Love JA. In Handbook of Metathesis Vol. 2:Grubbs RH. Wiley-VCH; Weinheim: 2003. p.296-322 - 9
Evans DA.Gauchet-Prunet JA. J. Org. Chem. 1993, 58: 2446 - 10a
Petrier C.Luche JL. J. Org. Chem. 1985, 50: 910 - 10b
Einhorn C.Luche JL. J. Organomet. Chem. 1987, 322: 177 - 10c
Chattopadhyay A. J. Org. Chem. 1996, 61: 6104 - 11
Dess PB.Martin JC. J. Am. Chem. Soc. 1978, 100: 300 - 12a
Keck GE.Wager CA. Org. Lett. 2000, 2: 2307 - 12b
Keck GE.Wager CA.Sell T.Wager T. S. J. Org. Chem. 1999, 64: 2172