Abstract
Some new substituted mono-, di-, and tricyclic furans were prepared catalytically from commercial and readily available starting materials via palladium-mediated sequential C-C and C-O bond formation in a single operation.
Key words
furan - domino reaction - palladium catalyst - allylic substitution
References
1a Rahmathullah SM.
Hall JE.
Bender BC.
McCurdy DR.
Tidwell RR.
Boykin DW.
J. Med. Chem.
1999,
42:
3994
1b Di Florio R.
Rizzacasa MA.
J. Org. Chem.
1998,
63:
8595
1c Hudlicky T.
Rulin F.
Lovelace TC.
Reed JW. In Studies in Natural Products Chemistry, Stereoselective Synthesis
part B, Vol. 3:
.
Elsevier Science;
Amsterdam:
1989.
p.3-72
2a Lockhart DJ, Patel HK, Mehta SA, Milanov ZV, Grotzfeld RM, and Lai AG. inventors; PCT Int. Appl. WO 2004110357 A2.
; Chem. Abstr. , 142, 69180
2b Castro-Hermida JA.
Gomez-Couso H.
Ares-Mazas ME.
Gonzalez-Bedia MM.
Castaneda-Cancio N.
Otero-Espinar FJ.
Blanco-Mendez J.
J. Pharm. Sci.
2004,
93:
197
2c Anbazhagan M.
Boykin DW.
Heterocycl. Commun.
2003,
9:
117
3a Nizamuddin GM.
Srivastava MK.
J. Sci. Ind. Res.
1999,
58:
1017
3b Ito H, Takeshiba H, Ota H, and Kato S. inventors; Jpn. Kokai Tokkyo Koho JP 10114765.
; Chem. Abstr. , 129, 24492
3c Venters K.
Trusuele M.
Rozhkova N.
Lukevics E.
Latv. PSR zinat. Akad. Vest.
1990,
10:
116
4a Kraft P.
Bajgrowicz JA.
Denis C.
Fráter G.
Angew. Chem. Int. Ed.
2000,
39:
2980
4b Harris EC, and Fayter RC. inventors; US 4681703.
; Chem. Abstr.
, 110, 23713
5a Kraus GA.
Wan Z.
Synlett
1997,
1259
5b Chan WH.
Lee AWM.
Chan ETT.
J. Chem. Soc., Perkin Trans. 1
1992,
945
5c Marshall JA.
Robinson ED.
J. Org. Chem.
1990,
55:
3450
5d Garst ME.
Spencer TA.
J. Org. Chem.
1983,
48:
2442
5e Wenkert E.
Heterocycles
1980,
14:
1703
5f Bartlett S.
Chambers RD.
Kelly NM.
Tetrahedron Lett.
1980,
21:
1891
6a Mandai T.
Hashio S.
Goto J.
Kawada M.
Tetrahedron Lett.
1981,
22:
2187
6b Hayashi T.
Ito Y.
Tetrahedron Lett.
1988,
29:
669
6c Yoshizaki H.
Satoh H.
Sato Y.
Nukui S.
Shibasaki M.
Mori M.
J. Org. Chem.
1995,
60:
2016
7 Lancaster M.
Green Chemistry
Royal Society of Chemistry;
Cambridge:
2002.
8 Heumann A.
Réglier M.
Tetrahedron
1996,
52:
9289
9a Trost BM.
Acc. Chem. Res.
1996,
29:
355
9b Trost BM.
Van Vranken D.
Chem. Rev.
1996,
96:
395
10a Trost BM.
Tanimori S.
Dunn PT.
J. Am. Chem. Soc.
1997,
119:
2735
10b Shimizu I.
Ohashi Y.
Tsuji J.
Tetrahedron Lett.
1985,
26:
3049
10c Tanimori S.
Kirihata M.
Tetrahedron Lett.
2000,
41:
6785
10d Lhoste P.
Massacret M.
Sinou D.
Bull. Soc. Chim. Fr.
1997,
134:
343
11 Generally, the reaction was carried out with [Pd(η3 -C3 H5 )Cl]2 or Pd(dba)2 as palladium source and PPh3 or dppf as ligand in THF, CH2 Cl2 , or DCE at r.t. to 50 °C. When the substrate has an acetoxyl group as leaving group, a base, such as organic base or metal carbonate, was used to neutralize the generating acidic species, see reference 14.
12 Calculations were carried out using the AM1 method in Mac Spartan Plus Ver 2.0.4, Wavefunction, Inc.
13 meso -dihydrofuran 10 as substrate in palladium-catalyzed allylic substitution reactions, see: Trost BM.
Crawley ML.
Chem. Rev.
2003,
103:
2921
14 Tanimori S.
Kato Y.
Kirihata M.
Synthesis
2004,
2103
15 Vinogradov MG.
Kondorskii AE.
Nikishin GI.
Synthesis
1988,
60
16a Lee YR.
Hwang JC.
Eur. J. Org. Chem.
2005,
1568
16b Alexiou I.
Gogonas EP.
Hadjiarapoglou LP.
Synlett
1999,
1925
16c Nair V.
Mathew J.
Nair LG.
Synth. Commun.
1996,
26:
4531
16d Nair V.
Mathew J.
J. Chem. Soc., Perkin Trans. 1
1995,
187
