Abstract
Copper-catalyzed reaction of 4-cyclopentene-1,3-diol monoacetate with ArCH2 MgCl afforded 4-arylmethyl-2-cyclopenten-1-ols regioselectively. Subsequent cleavage of the cyclopentene ring followed by functional group manipulation provided the key β-arylmethyl-γ-butyrolactones for the synthesis of lignans. In addition, synthesis of the rolipram lactone intermediate was accomplished.
Key words
allylations - γ-butyrolactone - copper - enterolactone - Grignard reactions
References
1a Ward RS.
Nat. Prod. Rep.
1999,
16:
75
1b Ward RS.
Nat. Prod. Rep.
1997,
14:
43
2a Tomioka K.
Ishiguro T.
Koga K.
J. Chem. Soc., Chem. Commun.
1979,
652
2b Tomioka K.
Ishiguro T.
Iitaka Y.
Koga K.
Tetrahedron
1984,
40:
1303
2c Tomioka K.
Mizuguchi H.
Koga K.
Chem. Pharm. Bull.
1982,
30:
4304
3a Moritani Y.
Fukushima C.
Ukita T.
Miyagishima T.
Ohmizu H.
Iwasaki T.
J. Org. Chem.
1996,
61:
6922
3b Moritani Y.
Fukushima C.
Miyagishima T.
Ohmizu H.
Iwasaki T.
Bull. Chem. Soc. Jpn.
1996,
69:
2281
4a Charlton JL.
Chee G.-L.
Can. J. Chem.
1997,
75:
1076
4b de Vanderlei JML.
Coelho F.
Almeida WP.
Synth. Commun.
1998,
28:
3047
4c Sibi MP.
Liu P.
Johnson MD.
Can. J. Chem.
2000,
78:
133
4d Sibi MP.
Liu P.
Ji J.
Hajra S.
Chen J.-x.
J. Org. Chem.
2002,
67:
1738
5a Shao L.
Miyata S.
Muramatsu H.
Kawaon H.
Ishii Y.
Saburi M.
Uchida Y.
J. Chem. Soc., Perkin Trans. 1
1990,
1441
5b Morimoto T.
Chiba M.
Achiwa K.
Tetrahedron
1993,
49:
1793
5c Kamlage S.
Sefkow M.
Pool-Zobel BL.
Peter MG.
Chem. Commun.
2001,
331
5d Kamlage S.
Sefkow M.
Zimmermann N.
Peter MG.
Synlett
2002,
77
5e Hughes G.
Kimura M.
Buchwald SL.
J. Am. Chem. Soc.
2003,
125:
11253
6a Itoh T.
Chika J.
Takagi Y.
Nishiyama S.
J. Org. Chem.
1993,
58:
5717
6b Shiotani S.
Okada H.
Yamamoto T.
Nakamata K.
Adachi J.
Nakamoto H.
Heterocycles
1996,
43:
113
6c Wang B.
Zhang H.
Wang W.
Bioorg. Med. Chem. Lett.
1996,
6:
945
6d Chenevert R.
Mohammadi-Ziarani G.
Caron D.
Dasser M.
Can. J. Chem.
1999,
77:
223
6e Caro Y.
Masaguer F.
Ravina E.
Tetrahedron: Asymmetry
2001,
12:
1723
7a Yoda H.
Kitayama H.
Katagiri T.
Takabe K.
Tetrahedron
1992,
48:
3313
7b van Oeveren A.
Jansen JFGA.
Feringa BL.
J. Org. Chem.
1994,
59:
5999
7c Brinksma J.
van der Deen H.
van Oeveren A.
Feringa BL.
J. Chem. Soc., Perkin Trans. 1
1998,
4159
8a Posner GH.
Kogan TP.
Haines SR.
Frye LL.
Tetrahedron Lett.
1984,
25:
2627
8b Brown E.
Daugan A.
Tetrahedron Lett.
1986,
27:
3719
8c Asaoka M.
Fujii N.
Shima K.
Takei H.
Chem. Lett.
1988,
805
8d Kosugi H.
Tagami K.
Takahashi A.
Kanna H.
Uda H.
J. Chem. Soc., Perkin Trans. 1
1989,
935
8e Brown E.
Daugan A.
Tetrahedron
1989,
45:
141
8f Takano S.
Ohashi K.
Sugihara T.
Ogasawara K.
Chem. Lett.
1991,
203
8g Koch SSC.
Chamberlin AR.
J. Org. Chem.
1993,
58:
2725
8h Honda T.
Kimura N.
Sato S.
Kato D.
Tominaga H.
J. Chem. Soc., Perkin Trans. 1
1994,
1043
8i Gagnon R.
Grogan G.
Groussain E.
Pedragosa-Moreau S.
Richardson PF.
Roberts SM.
Willetts AJ.
Alphand V.
Lebreton J.
Furstoss R.
J. Chem. Soc., Perkin Trans. 1
1995,
2527
8j Bode JW.
Doyle MP.
Protopopova MN.
Zhou Q.-L.
J. Org. Chem.
1996,
61:
9146
8k Pelter A.
Ward RS.
Abd-el-Ghani A.
J. Chem. Soc., Perkin Trans. 1
1996,
1353
8l Doyle MP.
Hu W.
Valenzuela MV.
J. Org. Chem.
2002,
67:
2954
9 Yamauchi S.
Machi M.
Kinoshita Y.
Biosci. Biotechnol. Biochem.
1999,
63:
1453
10a Ito M.
Murugesh MG.
Kobayashi Y.
Tetrahedron Lett.
2001,
42:
423
10b Ito M.
Matsuumi M.
Murugesh MG.
Kobayashi Y.
J. Org. Chem.
2001,
66:
5881
11a Kobayashi Y.
Curr. Org. Chem.
2003,
7:
133
11b Ainai T.
Matsuumi M.
Kobayashi Y.
J. Org. Chem.
2003,
68:
7825
12a Sugai T.
Mori K.
Synthesis
1988,
19
12b Laumen K.
Schneider MP.
J. Chem. Soc., Chem. Commun.
1986,
1298
13 Attempted reactions of TBS ether 13 with acidic H5 IO6 and of the triol with NaIO4 in place of KIO4 gave mixtures of products.
14 The observed specific rotation of the enterolactone dimethyl ether 15 in comparison with the reported values indicates no significant loss in enantiomeric purity at the carbon bearing the benzyl group during the ozonolysis and subsequent reduction of the intermediate (aldehyde).
15a Honda T.
Ishikawa F.
Kanai K.
Sato S.
Kato D.
Tominaga H.
Heterocycles
1996,
42:
109
15b Braun M.
Unger C.
Opdenbusch K.
Eur. J. Org. Chem.
1998,
2389
16a Mulzer J.
Zuhse R.
Schmiechen R.
Angew. Chem., Int. Ed. Engl.
1992,
31:
870
16b Meyers AI.
Snyder L.
J. Org. Chem.
1993,
58:
36
16c Diaz A.
Siro JG.
García-Navío JL.
Vaquero JJ.
Alvarez-Builla J.
Synthesis
1997,
559
16d Anada M.
Mita O.
Watanabe H.
Kitagaki S.
Hashimoto S.
Synlett
1999,
1775
16e Barluenga J.
Fernandez-Rodriguez MA.
Aguilar E.
Fernandez-Mari F.
Salinas A.
Olano B.
Chem.-Eur. J.
2001,
3533
16f Barnes DM.
Ji J.
Fickes MG.
Fitzgerald MA.
King SA.
Morton HE.
Plagge FA.
Preskill M.
Wagaw SH.
Wittenberger SJ.
Zhang J.
J. Am. Chem. Soc.
2002,
124:
13097
16g Yoon CH.
Nagle A.
Chen C.
Gandhi D.
Jung KW.
Org. Lett.
2003,
5:
2259
17a 1 with PhMgCl and CuCN (cat.) proceeded with high regioselectivity (93:7) in good yield, while reaction with PhMgBr were less selective (70:30). See: Ainai T.
Ito M.
Kobayashi Y.
Tetrahedron Lett.
2003,
44:
3983
17b In the present reaction, halogen-ligand exchange (Br to Cl) prior to reaction with monoacetate 1 is probably involved.
