7
6
.
Recent example: Miles, W. H.; Cohen, E. M.; Naimoli, B. J.
Compound 4j was prepared by the same procedure as that for
a, under the reaction conditions specified in Table 3 (entry 10);
ACCEPTED MANUSCRIPT
Synth. Commun. 2013, 43, 1980-1991.
Unoh, Y.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2013,
8, 5096-5102.
4
7
.
crystallized from toluene/hexanes; colourless crystals (65%); mp
7
1
7
2
8–80 °C; H NMR (CDCl ): δ = 1.45 (s, 9H), 1.93 (m, 2H),
3
8. Jing, C.; Xing, D.; Qian, Y.; Shi, T.; Zhao, Y.; Hu, W. Angew.
Chem. Int. Ed. 2013, 52, 9289-9292.
9. Some recent examples: (a) Tolstoluzhsky, N.; Nikolaienko, P.;
Gorobets, N.; Van der Eycken, E. V.; Kolos, N. Eur. J. Org.
.29 (t, J = 7.2 Hz, 2H), 2.73 (t, J = 6.9 Hz, 2H), 6.69 (d, J = 15.9
13
Hz, 1H), 7.13 (d, J = 15.9 Hz, 1H), 10.67 (bs, 1H); C NMR
CDCl ): δ = 18.9, 28.1, 34.3, 40.5, 80.7, 129.9, 140.8, 170.2,
(
1
3
+
Chem. 2013, 5364-5369; (b) Ghidu, V. P.; Ilies, M. A.; Cullen, T.;
Pollet, R.; Abou-Gharbia, M. Bioorg. Med. Chem. Lett. 2011, 21,
59-261; (c) Kaczanowska, K.; Eickhoff, H.; Albert, K.;
Wiesmüller, K.-H.; Schaffner, A.-P. J. Heterocyclic Chem. 2011,
8, 792-798.
72.6, 198.8; HRMS calcd for C H O (M+H) : 243.1227;
12 18 5
found: 243.1226.
2
4
.25. (2E,9E)-4,8-Dioxoundeca-2,9-dienedioic acid (4l)
4
1
0. Illustrative examples: (a) Tiruveedhula, V. V. N. P. B.;
Witzigmann, C. M.; Verma, R.; Kabir, M. S.; Rott, M.; Schwan,
W. R.; Medina-Bielski, S.; Lane, M.; Close, W.; Polanowski, R.
L.; Sherman, D.; Monte, A.; Deschamps, J. R.; Cook, J. M.
Bioorg. Med. Chem. 2013, 21, 7830-7840; (b) Sunnam, S. K.;
Prasad, K. R. Synthesis 2013, 45, 1991-1996; (c) Li, X.; Liu, N.;
Zhang, H.; Knudson, S. E.; Li, H.-J.; Lai, C.-T.; Simmerling, C.;
Slayden, R. A.; Tonge, P. J. ACS Med. Chem. Lett. 2011, 2, 818-
823; (d) Chakor, N.; Dallavalle, S.; Musso, L.; Moretti, M.
Tetrahedron Lett. 2008, 49, 5056-5058; (e) Kim, D.; Lee, J.;
Shim, P. J.; Lim, J. I.; Jo, H.; Kim, S. J. Org. Chem. 2002, 67,
Compound 4l was prepared by the same procedure as that for
a, under the reaction conditions specified in Table 3 (entry 12);
4
DBU was added over 30 min; the product precipitated upon
quenching with 1M H SO and cooling; white powder (44%); mp
2
4
1
2
2
1
3
10 °C; H NMR (DMSO-d ): δ =1.74 (quint, J = 7.2 Hz, 2H),
6
.74 (t, J = 7.2 Hz, 4H), 6.61 (d, J = 16.2 Hz, 2H), 6.87 (d, J =
13
6.2 Hz, 2H), 12.98 (bs, 2H); C NMR (DMSO-d ): δ = 17.3,
6
9.4, 131.4, 139.2, 166.6, 200.0; HRMS calcd for C H O
M+H) : 241.0712; found: 241.0752.
11
12
6
+
(
7
64-771.
4
.26. (E)-3-(3-Oxocyclohex-1-enyl)acrylic acid (4m)
11. Illustrative examples: (a) Bianchi, M.; Butti, A.; Christidis, Y.;
Perronnet, J.; Barzaghi, F.; Cesana, R.; Nencioni, A. Eur. J. Med.
Chem 1988, 23, 45-52; (b) Kameo, K.; Ogawa, K.; Takeshita, K.;
Nakaike, S. ; Tomisawa, K.; Sota, K. Chem. Pharm. Bull. 1988,
Compound 4m was prepared by the same procedure as that for
a, under the reaction conditions specified in Table 3 (entry 13);
4
3
6, 2050-2060.
12. (a) Kawashima, M.; Sato, T.; Fujisawa, T. Bull. Chem. Soc. Jpn.
988, 61, 3255-3264; (b) Kalita, D.; Khan, A. T.; Barua, N. C.;
purified by flash chromatography on silica gel (CH Cl /MeOH =
9
2
2
1
8/2 + 0.5% AcOH); white powder (40%); mp 214 °C; H NMR
1
(
(
DMSO-d ): δ = 1.95 (m, 2H), 2.35 (m, 2H), 2.50 (m, 2H), 6.22
s, 1H), 6.32 (d, J = 15.9 Hz, 1H), 7.33 (d, J = 15.9 Hz, 1H);
6
Bez, G. Tetrahedron 1999, 55, 5177-5184; (c) Rao, K. S.; Reddy,
D. S.; Mukkanti, K.; Pal, M.; Iqbal, J. Tetrahedron Lett. 2006, 47,
13
C
6
623-6626.
13. (a) Obrecht, D.; Weiss, B. Helv. Chim. Acta 1989, 72, 117-122;
b) Sonye, J. P.; Koide, K. J. Org. Chem. 2007, 72, 1846-1848.
NMR (DMSO-d ): δ = 21.7, 24.1, 37.3, 125.3, 131.7, 143.9,
1
1
6
+
54.6, 166.9, 199.3; HRMS calcd for C H O (M+H) :
9 10 3
(
67.0708; found: 167.0694.
1
4. Suh, Y.-G.; Seo, S.-Y.; Jung, J.-K.; Park, O.-H.; Jeon, R.-O.
Tetrahedron Lett. 2001, 42, 1691-1694.
Acknowledgments
15. (a) Shet, J.; Desai, V.; Tilve, S. Synthesis 2004, 1859-1863; (b)
McLaughlin, E. C.; Choi, H.; Wang, K.; Chiou, G.; Doyle, M. P.
J. Org. Chem. 2009, 74, 730-738.
This work was supported by the Slovak Research and
Development Agency under contract No. LPP-0457-11.
1
6. (a) Kobayashi, Y.; Watatani, K.; Kikori, Y.; Mizojiri, R.
Tetrahedron Lett. 1996, 37, 6125-6128; (b) Kobayashi, Y.;
Nakano, M.; Kumar, G. B.; Kishihara, K. J. Org. Chem. 1998, 63,
7505-7515; (c) Ballini, R.; Bosica, G. J. Nat. Prod. 1998, 61, 673-
References and notes
6
1
74; (d) Annangudi, S. P.; Sun, M.; Salomon, R. G. Synlett 2005,
468-1470.
1
.
(E)-4-Oxohexadec-2-enoic acid: Eschen-Lippold, L.; Draeger, T.;
Teichert, A.; Wessjohann, L.; Westermann, B.; Rosahl, S.;
Arnold, N. J. Agric. Food Chem. 2009, 57, 9607-9612; Patulolide
A: Sekiguchi, J.; Kuroda, H.; Yamada, Y.; Okada, H. Tetrahedron
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1
1
7. Våbenø, J.; Brisander, M.; Lejon, T.; Luthman, K. J. Org. Chem.
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8. (a) Gardianová, M.; Slížik, Ľ.; Koreňová, A.; Považanec, F.;
Berkeš, D. Chem. Pap. 2013, 67, 92-100; (b) Ďuriš, A.;
2
Wiesenganger, T.; Moravčíková, D.; Baran, P.; Kožíšek, J.; Daïch,
A.; Berkeš, D. Org. Lett. 2011, 13, 1642-1645; (c) Jakubec, P.;
Berkeš, D. Tetrahedron: Asymmetry 2010, 21, 2807-2815; (d)
Jakubec, P.; Petráš, P.; Ďuriš, A.; Berkeš, D. Tetrahedron:
Asymmetry 2010, 21, 69-74; (e) Berkeš, D.; Koreňová, A.; Šafář,
P.; Horváthová, H.; Prónayová, N. Cent. Eur. J. Chem. 2007, 5,
Pummangura, S.; Chaichantipyuth, C.; Patarapanich, C.; Fanwick,
P. E.; Chang, C.-J.; Mclaughlin, J. L. Tetrahedron 1990, 46, 5043-
5
054; Pyrenophorin: Nozoe, S.; Hirai, K.; Tsuda, K.; Ishibashi,
K.; Shirasaka, M.; Grove, J. F. Tetrahedron Lett. 1965, 6, 4675-
677; Macrosphelide B: Hayashi, M.; Kim, Y.-P.; Hiraoka, H.;
4
Natori, M.; Takamatsu, S.; Kawakubo, T.; Masuma, R.;
6
88-705; (f) Jakubec, P.; Berkeš, D.; Šiška, R.; Gardianová, M.;
Komiyama, K.; Omura, S. J. Antibiot. 1995, 48, 1435-1439;
Cytochalasin A: Aldridge, D. C.; Armstrong, J. J.; Speake, R. N.;
Turner, W. B. J. Chem. Soc. (C) 1967, 1667-1676.
Považanec, F. Tetrahedron: Asymmetry 2006, 17, 1629-1637; (g)
Berkeš, D.; Kolarovič, A.; Manduch, R.; Baran, P.; Považanec, F.
Tetrahedron: Asymmetry 2005, 16, 1927-1934; (h) Kolarovič, A.;
Berkeš, D.; Baran, P.; Považanec, F. Tetrahedron Lett. 2005, 46,
2
3
.
.
For illustrative examples, see: (a) Zhao, S.; Lin, J.-B.; Zhao, Y.-
Y.; Liang, Y.-M.; Xu, P.-F. Org. Lett. 2014, 16, 1802-1805; (b)
Wang, Z.; Chen, D.; Yang, Z.; Bai, S.; Liu, X.; Lin, L.; Feng, X.
Chem. Eur. J. 2010, 16, 10130-10136; (c) Lu, H.-H.; Wang, X.-F.;
Yao, C.-J.; Zhang, J.-M.; Wu, H.; Xiao, W.-J. Chem. Commun.
9
75-978; (i) Kolarovič, A.; Berkeš, D.; Baran, P.; Považanec, F.
Tetrahedron Lett. 2001, 42, 2579-2582.
1
2
9. Dal Pozzo, A.; Acquasaliente, M.; Buraschi, M. Synthesis 1984,
9
26-927.
2
009, 4251-4253.
0. (a) Rodriguez, M.; Bruno, I.; Cini, E.; Marchetti, M.; Taddei, M.;
Gomez-Paloma, L. J. Org. Chem. 2006, 71, 103-107; (b) Shapiro,
G.; Buechler, D.; Hennet, S. Tetrahedron Lett. 1990, 31, 5733-
For illustrative examples, see: (a) Žari, S.; Kudrjashova, M.; Pehk,
T.; Lopp, M.; Kanger, T. Org. Lett. 2014, 16, 1740-1743; (b) Zhu,
X.-Y., Chen, J.-R.; Lu, L.-Q.; Xiao, W.-J. Tetrahedron 2012, 68,
5
736.
6
032-6037; (c) Jakubec, P.; Berkeš, D.; Kolarovič, A.; Považanec,
2
2
1. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.;
F. Synthesis 2006, 4032-4040; (d) Drakulić, B. J.; Juranić, Z. D.;
Stanojković, T. P.; Juranić, I. O. J. Med. Chem. 2005, 48, 5600-
Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984,
2
5, 2183-2186.
5
603.
2. (a) Wenkert, E.; Guo, M.; Lavilla, R.; Porter, B.; Ramachandran,
K.; Sheu, J.-H. J. Org. Chem. 1990, 55, 6203-6214; (b) Maloney,
K. M.; Chung, J. Y. L. J. Org. Chem. 2009, 74, 7574-7576; (c)
Mikołajczyk, M.; Mikina, M. J. Org. Chem. 1994, 59, 6760-6765.
For a very recent report on chemoselective synthesis of β-
4
5
.
.
Illustrative example: Bai, S.; Liu, X.; Wang, Z.; Cao, W.; Lin, L.;
Feng, X. Adv. Synth. Catal. 2012, 354, 2096-2100.
Dong, X.; Liang, L.; Li, E.; Huang, Y. Angew. Chem. Int. Ed.
2
015, 54, 1621-1624.