Abstract
An efficient synthesis of bis-nor Wieland-Miescher ketone and its derivatives starting from commercially available 2-allyl-2-methylcyclopenta-1,3-dione is described.
Key words
alkylation - carbocycles - cyclization - epoxidation - Wittig reaction
References
1a Shah N.
Scanlan TS.
Bioorg. Med. Chem. Lett.
2004,
14:
5199
1b Kende AS.
Deng W.-P.
Zhong M.
Guo X.-C.
Org. Lett.
2003,
5:
1785
1c Aav R.
Kanger T.
Pehk T.
Lopp M.
Synlett
2000,
529
1d Inomata K.
Barrague M.
Paquette LA.
J. Org. Chem.
2005,
70:
533
1e Mulzer J.
Kaselow U.
Graske K.-D.
Kühne H.
Sieg A.
Martin HJ.
Tetrahedron
2004,
60:
9599
1f Subburaj K.
Okamoto S.
Sato F.
J. Org. Chem.
2002,
67:
1024
1g Mukai C.
Kobayashi M.
Kim IJ.
Hanaoka M.
Tetrahedron
2002,
58:
5225
2 Ramachandran S.
Newman MS.
Org. Synth. Coll. Vol. V
Wiley;
New York:
1973.
p.486
3 Buchschahcer P.
Fürst A.
Gutzwiller J.
Org. Synth. Coll. Vol. VII
Wiley;
New York:
1990.
p.368
4a Dauben WG.
Hart DJ.
J. Org. Chem.
1977,
42:
3787
4b Aav R.
Kanger T.
Pehk T.
Lopp M.
Phosphorus, Sulfur Silicon Relat. Elem.
2005,
180:
1739
5 NakashitaY .
Watanabe T.
Benkert E.
Lorenzi-Riatsch A.
Hesse M.
Helv. Chim. Acta
1984,
67:
1204
6 Geetha G.
Raju N.
Rajagopalan K.
Swaminathan S.
Indian J. Chem.
1981,
20B:
238
7 Brooks DW.
Woods KW.
J. Org. Chem.
1987,
52:
2036
8a Kinoshita A.
Mori M.
Chem. Lett.
1994,
1475
8b Mori M.
Isono .
Kaneta N.
Shibasaki M.
J. Org. Chem.
1993,
58:
2972
9a Trost BM.
Curran DP.
J. Am. Chem. Soc.
1980,
102:
5699
9b Trost BM.
Curran DP.
Tetrahedron Lett.
1981,
22:
4929
10 6-Allyl-6-methyldihydro-2H- pyran-2,5 (6H )-dione: 1 H NMR (CDCl3 ): δ = 5.72 (m, 1 H, =CH), 5.13 and 5.15 (m, 2 H, =CH2 ), 2.84 and 2.88 (m, 2 H, H-3), 2.73 and 2.60 (m, 2 H, H-4), 2.65 and 2.45 (tdd each, 2 H, J = 0.9, 0.9, 7.4, 14.1 Hz, CH
2 CH=CH2 ), 1.48 (s, 3 H, CH3 ). 13 C NMR (CDCl3 ): δ = 207.23 (C-5), 169.24 (C-2), 130.35 (=CH), 121.06 (=CH2 ), 88.71 (C-6), 43.20 (C H2 CH=CH2 ), 33.96 (C-4), 28.04 (C-3), 24.92 (CH3 ).
11 Borowitz IJ.
Parnes H.
Lord E.
Yee KC.
J. Am. Chem. Soc.
1972,
94:
6817
12 Borowitz IJ.
Grossman LJ.
Tetrahedron Lett.
1962,
471
13 Alternatively, a crystalline phosphonium salt can be isolated by filtration remaining by-product into solution. However, this isolation decreases the overall yield of compound 2 from 79% to 64%.
14 Paju A.
Kanger T.
Pehk T.
Müürisepp A.-M.
Lopp M.
Tetrahedron: Asymmetry
2002,
13:
2439
15 Paju A.
Kanger T.
Pehk T.
Lindmaa R.
Müürisepp A.-M.
Lopp M.
Tetrahedron: Asymmetry
2003,
14:
1565
16 Paju A.
Kanger T.
Niitsoo O.
Pehk T.
Müürisepp A.-M.
Lopp M.
Tetrahedron: Asymmetry
2003,
14:
2393
17 Paju A.
Kanger T.
Pehk T.
Eek M.
Lopp M.
Tetrahedron
2004,
60:
9081
18a Fujita M.
Shindo M.
Shishido K.
Tetrahedron Lett.
2005,
46:
1269
18b Yao S.
Johannsen M.
Hazell RG.
Jørgensen KA.
J. Org. Chem.
1998,
63:
118
19 Mandelt K.
Fitjer L.
Synthesis
1998,
1523
20 Navarro-Eisenstein AM.
Vasquez PC.
Franklin PJ.
Baumstark AL.
Heterocycl. Commun.
2003,
9:
449
