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 2011(16): 2671-2683
DOI: 10.1055/s-0030-1260115
DOI: 10.1055/s-0030-1260115
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Limno-CP: A Natural-Product-Inspired 5-Aryl-3(2H)-furanone as Scaffold for a Library of α-Modified Enones
Further Information
Received
29 April 2011
Publication Date:
14 July 2011 (online)
Publication History
Publication Date:
14 July 2011 (online)
Abstract
A library of 5-aryl-3(2H)-furanones that are modified in the α-position of the α,β-unsaturated carbonyl system was prepared via simple one- to three-step transformations from one common scaffold. The ¹³C NMR characterization of the enone system showed a strong influence of the α-substituents, especially on the shifts of the α- and β-carbon atoms. Probing the addition chemistry of nucleophiles versus our α-modified enones, a 1,2-addition-elimination was found, but no 1,4-addition.
Key words
furanones - substituent effects - enones - spiro compounds - 1,2-addition-elimination
- Supporting Information for this article is available online:
- Supporting Information
- 1
Jerris PJ.Smith AB. J. Org. Chem. 1981, 46: 577 - 2
Le Quesne PW.Levery SB.Menachery MD.Brennan TF.Raffauf RF. J. Chem. Soc., Perkin Trans. 1 1978, 1572 - 3
Kupchan SM.Sigel CW.Matz MJ.Gilmore CJ.Bryan RF. J. Am. Chem. Soc. 1976, 98: 2295 - 4
Ishikawa M.Ninomiya T.Akabane H.Kushida N.Tsujiuchi G.Ohyama M.Gomi S.Shito K.Murata T. Bioorg. Med. Chem. Lett. 2009, 19: 1457 - 5 For an overview about 3(2H)-furanones, see:
Haug TT.Kirsch SF. In Targets in Heterocyclic Systems Vol. 13:Attanasi OA.Spinelli D. Royal Society of Chemistry; London: 2009. p.57 - 6
Amslinger S. ChemMedChem 2010, 5: 351 - 7
Lawrence NJ.Patterson RP.Ooi L.-L.Cook D.Ducki S. Bioorg. Med. Chem. Lett. 2006, 16: 5844 - 8
Blum G.Gazit A.Levitzki A. Biochemistry 2000, 39: 15705 - 9
Honda T.Gribble GW.Suh N.Finlay HJ.Rounds BV.Bore L.Favaloro FG.Wang Y.Sporn MB. J. Med. Chem. 2000, 43: 1866 -
10a
Honda T.Rounds BV.Bore L.Finlay HJ.Favaloro FG.Suh N.Wang YP.Sporn MB.Gribble GW. J. Med. Chem. 2000, 43: 4233 -
10b
Honda T.Honda Y.Favaloro FG.Gribble GW.Suh N.Place AE.Rendi MH.Sporn MB. Bioorg. Med. Chem. Lett. 2002, 12: 1027 -
10c
Dinkova-Kostova AT.Liby KT.Stephenson KK.Holtzclaw WD.Gao XQ.Suh N.Williarrli C.Risingsong R.Honda T.Gribble GW.Sporn MB.Talalay P. Proc. Natl. Acad. Sci. U.S.A. 2005, 102: 4584 -
10d
Wang S.-J.Yan J.-F.Hao D.Niu X.-W.Cheng M.-S. Molecules 2007, 12: 885 -
10e
Wang J.Wang S.Song D.Zhao D.Sha Y.Jiang Y.Jing Y.Cheng M. Chem. Biol. Drug Des. 2009, 73: 511 -
10f
Levitzki A.Gazit A. Science 1995, 267: 1782 -
10g
Levitzki A.Mishani E. Annu. Rev. Biochem. 2006, 75: 93 - 11
Dinkova-Kostova AT.Talalay P. Mol. Nutr. Food Res. 2008, 52: S128 - 12
Jang DS.Su BN.Pawlus AD.Jones WP.Kleps RA.Bunyapraphatsara N.Fong HHS.Pezzuto JM.Kinghorn AD. J. Nat. Prod. 2005, 68: 1134 - 13
Shao X.Dolder M.Tamm C. Helv. Chim. Acta 1990, 73: 483 - 14
Smith AB.Levenberg PA.Jerris PJ.Scarborough RM.Wovkulich PM. J. Am. Chem. Soc. 1981, 103: 1501 - 15
Casnati G.Quilico A.Ricca A.Finzi PV. Tetrahedron Lett. 1966, 7: 233 -
16a
Sher F.Isidor JL.Taneja HR.Carlson RM. Tetrahedron Lett. 1973, 14: 577 -
16b
Kato K.Nouchi H.Ishikura K.Takaishi S.Motodate S.Tanaka H.Okudaira K.Mochida T.Nishigaki R.Shigenobu K.Akita H. Tetrahedron 2006, 62: 2545 -
16c
Kirsch SF.Binder JT.Liébert C.Menz H. Angew. Chem. Int. Ed. 2006, 45: 5878 -
16d
Bunnelle EM.Smith CR.Lee SK.Singaram SW.Rhodes AJ.Sarpong R. Tetrahedron 2008, 64: 7008 -
16e
Egi M.Azechi K.Saneto M.Shimizu K.Akai S. J. Org. Chem. 2010, 75: 2123 - 18
Shin SS.Byun Y.Lim KM.Choi JK.Lee K.-W.Moh JH.Kim JK.Jeong YS.Kim JY.Choi YH.Koh H.-J.Park Y.-H.Oh YI.Noh M .-S.Chung S.
J. Med. Chem. 2004, 47: 792 - 19
Solladié G.Pasturel-Jacopé Y.Maignan J. Tetrahedron 2003, 59: 3315 - 20
Parker W.Raphael RA.Wilkinson DI. J. Chem. Soc. 1958, 3871 - A corresponding enamine intermediate could be isolated from the cyclization of a very similar starting material with Et2NH in THF-H2O (9:1) in high yield. Mechanisms via 1,3-diketones, which involve a simple hydration of the triple bond typically require acids or mercury salts; see:
-
21a
Williams DR.Abbaspour A.Jacobson RM. Tetrahedron Lett. 1981, 22: 3565 -
21b
Saimoto H.Shinoda M.Matsubara S.Oshima K.Hiyama T.Nozaki H. Bull. Chem. Soc. Jpn. 1983, 56: 3088 - For the addition of CO2 via the formation of a 1,3-dioxolan-2-one to the 1,3-diketone, see:
-
21c
Inoue Y.Ohuchi K.Imaizumi S. Tetrahedron Lett. 1988, 29: 5941 -
21d
Kawaguchi T.Yasuta S.Inoue Y. Synthesis 1996, 1431 - 22
Ripka A,Shapiro G, andChesworth R. inventors; PCT Int. Appl. WO 2009158393 A1. ; Chem. Abstr. 2009, 152, 87491 - 23
Crone B.Kirsch SF. J. Org. Chem. 2007, 72: 5435 - 24
Chao ST, andVarma RK. inventors; US Patent 4243586. ; Chem. Abstr. 1981, 95, 98152 -
25a
Leanza WJ.Conbere JP.Rogers EF.Pfister K.
J. Am. Chem. Soc. 1954, 76: 1691 -
25b
You Z.Heiman AS.Chen M.Lee HJ. Steroids 2000, 65: 109 - 26
Paleta O.Pelter A.Kebrle J.Duda Z.Hajduch J. Tetrahedron 2000, 56: 3197 - 27
Trofimov BA.Shemyakina OA.Mal’kina AG.Ushakov IA.Kazheva ON.Alexandrov GG.Dyachenko OA. Org. Lett. 2010, 12: 3200 - 28
McNab H.Monahan LC. J. Chem. Soc., Perkin Trans. 1 1989, 419 - 29
Paquette LA.Liu Z.Ramsey C.Gallucci JC. J. Org. Chem. 2005, 70: 8154 - 30
Soorukram D.Knochel P. Org. Lett. 2007, 9: 1021 - 31
Paleta O.Duda Z.Hol A. Mendeleev Commun. 2001, 11: 17 - 32
Nyffeler PT.Durón SG.Burkart MD.Vincent SP.Wong C.-H. Angew. Chem. Int. Ed. 2004, 44: 192 - 33
Arvela RK.Leadbeater NE. J. Org. Chem. 2003, 68: 9122 - 34
Butora G.Jiao R.Parsons WH.Vicario PP.Jin H.Ayala JM.Cascieri MA.Yang L. Bioorg. Med. Chem. Lett. 2007, 17: 3636 - 35
Mull ES.Sattigeri VJ.Rodriguez AL.Katzenellenbogen JA. Bioorg. Med. Chem. 2002, 10: 1381 - 36
Takeda K.Kawanishi E.Nakamura H.Yoshii E. Tetrahedron Lett. 1991, 32: 4925 - 37
Costa AMBSRCS.Dean FM.Jones MA.Varma RS. J. Chem. Soc., Perkin Trans. 1 1985, 799 - 38
Shipe WD.Sorensen EJ. Org. Lett. 2002, 4: 2063 -
39a
Lin W.Chen L.Knochel P. Tetrahedron 2007, 63: 2787 -
39b
Thibonnet J.Anh Vu V.Bérillon L.Knochel P. Tetrahedron 2002, 58: 4787 - 40
Wang X.-j.Sun X.Zhang L.Xu Y.Krishnamurthy D.Senanayake CH. Org. Lett. 2005, 8: 305 - 41 The ratios were determined by 2D
NMR techniques including ROESY. The chemical shifts of vinylic protons
in 7 (see assignments in Figure 3) of α-Cl
products 31a, 31b were
assigned by comparison with 26a, 26b, 30a, 30b, 32a, 32b, and the literature, see:
Botta D.Mantica E.Castellani L.Dotelli G.Zetta L. Magn. Reson. Chem. 1998, 36: 885 - 42
Smith AB.Jerris PJ. Synth. Commun. 1978, 8: 421 - 43
Schmidt TJ. Bioorg. Med. Chem. 1997, 5: 645
References
For the acid-induced cyclization of 4-hydroxy-1,3-diketones no spirocyclic compound is reported. Examples for monocyclic compounds are given in Ref. 1.