H. Harkat et al. / Tetrahedron 65 (2009) 1871–1879
1879
4.7.3. (6E,60E)-6,60-(Ethane-1,2-diylidene)bis(tetrahydro-2H-
pyran-2-one) (7c)
7. (a) Takayama, H.; Ichikawa, T.; Kitajima, A. M.; Nonato, M. G.; Aimi, N. Chem.
Pharm. Bull. 2002, 50, 1303–1304; (b) Marquez, V. E.; Bloomberg, P. M. Acc.
Chem. Res. 2003, 36, 434–443.
8. Singh, S.; Malik, B. K.; Sharma, D. K. Int. J. Integrative Biol. 2007, 1, 72–87.
9. Hamer, D. H.; Bocklandt, S.; McHugh, L.; Chun, T.-W.; Blumberg, P. M.; Sigano,
D. M.; Marquez, V. E. J. Virol. 2003, 77, 10227–10236.
Hex-5-ynoic acid (80 mg, 0.72 mmol) gave dimer 7c (24 mg,
0.206 mmol) as a white solid, 30% yield. TLC Rf 0.60 (cyclohexane/
EtOAc 60%); mp 127.6 ꢀC; IR (neat) nmax 2951, 2921, 1791, 1734, 1700,
10. (a) Knight, D. M. Contemp. Org. Synth. 1994, 1, 287–315; (b) Collins, I. J. Chem.
Soc., Perkin Trans. 1 1999, 1377–1395; (c) Bru¨ckner, R. Curr. Org. Chem. 2001, 5,
679–7
1216,1109,1046, 876 cmꢁ1; 1H NMR (300 MHz, CDCl3)
d
5.78 (s, 2H),
18; (d) De Souza, M. V. N. Mini-Rev. Org. Chem. 2005, 2, 546–564.
2.63 (t, J¼6.6 Hz, 4H), 2.58 (t, J¼6.6 Hz, 4H), 1.91 (quint, J¼6.8 Hz,
4H); 13C NMR (75 MHz, CDCl3)
d 168.0, 150.1, 104.2, 30.7, 22.7, 18.0;
11. (a) Weibel, J.-M.; Blanc, A.; Pale, P. Chem. Rev. 2008, 108, 3149–3173; (b) Alvarez-
Corral, M.; Munoz-Dorado, M.; Rodriguez-Garcia, I. Chem. Rev. 2008, 108, 3174–
3198.
12. (a) Castulik, J.; Mazal, C. Tetrahedron Lett. 2000, 41, 2741–2744; (b) Bellina, F.;
Anselmi, C.; Rossi, R. Tetrahedron Lett. 2002, 43, 2023–2027; (c) Scheiper, B.;
Bonnekessel, M.; Krause, H.; Fu¨ rstner, A. J. Org. Chem. 2004, 69, 3943–3949.
13. (a) Lee, K. Y.; Kim, J. M.; Kim, J. N. Synlett 2003, 357–360; (b) Haase, C.; Langer, P.
Synlett 2005, 453–456.
HRMS: calcd for C12H12NaO2 [MþNa]þ 222.0898, found 222.1189.
4.8. Typical procedure for dimer formations catalyzed
by AuCl
14. (a) Bougalt, M. J. C.R. Acad. Sci. 1904, 139, 864–867; (b) Gevaza, Y. I.; Staninets,
V. I. Chem. Heterocycl. Compd. 1988, 24, 1073–1088; (c) Harding, K. E.; Tiner, T. H.
In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon:
See the typical procedure for the formation of enol lactones
from
u-acetylenic acids.
`
New York, NY, 1991; Vol. 4, p 363; (d) Harmange, J.-C.; Figadere, B. Tetrahedron:
Asymmetry 1993, 4, 1711–1754.
4.8.1. (5Z,50Z)-5,50-(Ethane-1,2-diylidene)bis(dihydrofuran-2(3H)-
one) (9a)
15. Hg catalysis: (a) Yamamoto, M. J. Chem. Soc., Perkin Trans. 1 1981, 582–587; (b)
Jellal, A.; Grimaldi, J.; Santelli, M. Tetrahedron Lett. 1984, 25, 3179–3181; (c)
Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459–5466;
Sofia, M. J.; Chakravarty, P. K. (d) Katzenellenbogen, J. A. J. Org. Chem. 1985, 50,
2331–2336; Pd catalysis: (e) Yanagihara, N.; Lambert, C.; Iritani, K.; Utimoto, K.;
Nozaki, H. J. Am. Chem. Soc. 1986, 108, 2753–2754; (f) Arcadi, A.; Cacchi, S.;
Marnelli, F. Tetrahedron Lett. 1992, 27, 3915–3918; (g) Bouyssi, D.; Gore´, J.;
Balme, G. Tetrahedron Lett. 1992, 33, 2811–2814; (h) Kotora, M.; Negishi, E.-i
Synthesis 1997, 121–128; (i) Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron Lett.
1998, 39, 3017–3020; Rh catalysis: (j) Chan, D. M. T.; Marder, T. B.; Milstein, D.;
Taylor, N. J. J. Am. Chem. Soc. 1987, 109, 6385–6388; (k) Elgafi, S.; Field, L. D.;
Messerle, B. A. J. Organomet. Chem. 2000, 607, 97–104.
Deca-4,6-diynedioic acid (60 mg, 0.31 mmol) gave dimer 9a
(34 mg, 0.175 mmol) as a white solid, 56% yield. TLC Rf 0.40 (cy-
clohexane/EtOAc 30%); mp 214–215 ꢀC (dec); IR (neat) nmax 2935,
1736, 1652, 1440, 1309, 1163, 1090, 919 cmꢁ1 1H NMR (300 MHz,
;
CD3CN)
d
5.52 (s, 2H), 2.89 (t, J¼9.0 Hz, 4H), 2.68–2.62 (m, 4H); 13
C
NMR (75 MHz, CD3CN)
d 175.1, 148.4, 97.1, 27.2, 24.7; HRMS: calcd
for C10H10NaO4 [MþNa]þ 217.0477, found 217.0471.
16. Ag catalysis: (a) Rammah, M. M.; Othman, M.; Ciamala, K.; Strohmann, C.;
Rammah, M. B. Tetrahedron 2008, 64, 3505–3516; Au catalysis: (b) Genin, E.;
Toullec, P. Y.; Antoniotti, S.; Brancour, C.; Genet, J.-P.; Michelet, V. J. Am. Chem. Soc.
2006,128, 3112–3113;(c)Genin,E.;Toullec, P. Y.;Marie,P.;Antoniotti,S.;Brancour,
C.; Genet, J.-P.; Michelet, V. ARKIVOC 2007, 5, 67–78; (d) Marchal, E.; Uriac, P.;
Legoin, B.;Toupet, L.;VandeWeghe. Tetrahedron2007, 63, 9979–9990;(e)Toullec,
P. Y.; Genin, E.; Antoniotti, S.; Genet, J.-P.; Michelet, V. Synlett 2008, 707–711.
17. (a) Pale, P.; Chuche, J. Tetrahedron Lett. 1987, 51, 6447–6448; (b) Chuche, J.;
Grandjean, D.; Pale, P. Bull. Soc. Chim. Belg. 1992, 101, 415–425; (c) Dalla, V.; Pale,
P. Tetrahedron Lett. 1994, 35, 3525–3528; (d) Dalla, V.; Pale, P. New J. Chem. 1999,
23, 803–805.
18. Harkat, H.; Weibel, J.-M.; Pale, P. Tetrahedron Lett. 2006, 47, 6273–6276.
19. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York,
NY, 1994.
20. Hofmeister, H.; Annen, K.; Laurent, H.; Wiechert, H. Angew. Chem., Int. Ed. Engl.
1984, 23, 727–729.
4.8.2. (5Z,50Z)-5,50-(Ethane-1,2-diylidene)bis(4,4-
dimethyldihydrofuran-2(3H)-one) (9b)
3,3,8,8-Tetramethyldeca-4,6-diynedioic acid (40 mg, 0.160 mmol)
gave dimer 9b (7 mg, 0.028 mmol) as a white solid, 18% yield. TLC Rf
0.45 (cyclohexane/EtOAc 30%); mp 171 ꢀC; IR (neat) nmax 2964, 2922,
1788, 1655, 1465, 1386, 1162, 1050 cmꢁ1; 1H NMR (300 MHz, CDCl3)
d
5.58 (s, 2H), 2.52 (s, 4H), 1.33 (s, 12H); 13C NMR (75 MHz, CDCl3)
172.9, 157.6, 95.8, 43.1, 39.1, 27.9; HRMS: calcd for C14H19LiO44
d
[MþLi]þ 257.1365, found 257.1409.
4.8.3. (6Z,60Z)-6,60-(Ethane-1,2-diylidene)bis(tetrahydro-2H-
pyran-2-one) (9c)
21. Dai, W.; Katzenellenbogen, J. A. J. Org. Chem. 1991, 56, 6893–6896.
22. Spencer, R. W.; Fat Tam, T.; Thomas, E.; Robinson, V. J.; Krantz, A. J. Am. Chem.
Soc. 1986, 108, 5589–5597.
23. Jefford, C. W.; Wang, Y. Chem. Commun. 1987, 20, 1513–1514.
24. (a) Colvin, E. Silicon in Organic Synthesis; Buttersworths: Boston, 1981; (b) The
Chemistry of Organosilicon Compounds: Part I and II; Pata¨ı, S., Rappoport, Z., Eds.;
Interscience: New York, NY, 1989.
Dodeca-5,7-diynedioic acid (50 mg, 0.16 mmol) gave dimer 9c
(12 mg, 0.054 mmol) as a thick colourless oil, 34% yield. TLC Rf 0.55
(cyclohexane/EtOAc 60%); IR (neat) nmax 2920, 1740, 1701, 1638,
1216, 1121, 1039 cmꢁ1
;
1H NMR (300 MHz, CDCl3)
d
5.72 (s, 2H),
2.65 (t, J¼6.8 Hz, 4H), 2.50 (t, J¼6.4 Hz, 4H), 1.87 (quint, J¼6.8 Hz,
4H); 13C NMR (75 MHz, CDCl3)
d 167.7, 147.4, 101.6, 30.7, 27.3, 18.7;
25. Nie, X.; Wang, G. J. Org. Chem. 2006, 71, 4734–4741.
HRMS: calcd for C12H14LiO4 [MþLi]þ 229.1052, found 229.1089.
26. Mindt, T. L.; Schibli, R. J. Org. Chem. 2007, 72, 10247–10250.
27. Sofia, M. J.; Chakravarty, P. K.; Katzenellenbogen, J. A. J. Org. Chem. 1983, 48,
3318–3325.
28. Hashmi, A. S. K.; Blanco, M. C.; Fisher, D.; Bats, J. W. Eur. J. Org. Chem. 2006,
1387–1489.
Acknowledgements
29. McCombs, J. D.; Blunt, J. W.; Chambers, M. V.; Munro, M. H. G.; Robinson, W. T.
Tetrahedron 1988, 45, 3179.
The authors thank the CNRS and the French Ministry of Research
for financial support. H.H. thanks the Algerian government for
fellowship.
30. For reports on Au(I)/Au(III) dichotomy in the synthesis of heterocycles, see: (a)
Sromek, A. W.; Rubina, M.; Gevorgyan, V. J. Am. Chem. Soc. 2005, 127, 10500–
10501; (b) Xia, Y.; Dudnik, A. S.; Gevorgyan, V.; Li, Y. J. Am. Chem. Soc. 2008, 130,
6940–6941; (c) Dudnik, A. S.; Sromek, A. W.; Rubina, M.; Kim, J. T.; Kel’in, A. V.;
Gevorgyan, V. J. Am. Chem. Soc. 2008, 130, 1440–1452.
References and notes
31. For recent reviews on Au(I)- and Au(III)-catalysis in organic synthesis, see: (a)
Shen, H. C. Tetrahedron 2008, 64, 3885–3903; (b) Li, Z.; Brouwer, C.; He, C. Chem.
Rev. 2008, 108, 3239–3265; (c) Jime´nez-Nu´ n˜ez, E.; Echavarren, A. M. Chem. Rev.
2008, 108, 3326–3350; (d) Arcadi, A. Chem. Rev. 2008, 108, 3266–3325; (e)
Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180–3211; (f) Bongers, N.; Norbert
Krause, N. Angew. Chem., Int. Ed. 2008, 47, 2178–2181; (g) Fu¨rstner, A.; Davies, P.
W. Angew. Chem., Int. Ed. 2008, 47, 3410–3449; (h) Widenhoefer, R. A.; Han, X.
Eur. J. Org. Chem. 2006, 4555–4563; (i) Hashmi, A. S. K.; Hutchings, G. J. Angew.
Chem., Int. Ed. 2006, 45, 7896–7936.
32. Behrens, O. K.; Corse, J.; Huff, D. E.; Jones, R. G.; Soper, Q. F.; Whitehead, C. W. J.
Biol. Chem. 1948, 175, 771–792.
33. Du, W.; Curran, D. P. Org. Lett. 2003, 5, 1765–1768.
34. Dunetz, J. R.; Danheiser, R. L. J. Am. Chem. Soc. 2005, 127, 5776–5777.
35. Kobayashi, A.; Yamashita, K. Agric. Biol. Chem. 1975, 39, 2247–2251.
36. Chapuis, C.; Bu¨ chi, G. H.; Wu¨ est, H. Helv. Chim. Acta 2005, 88, 3069–
3088.
1. For reviews, see: (a) Koch, S. S. C.; Chamberlin, A. R. In Studies in Natural
Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1995; Vol. 16,
pp 687–726; (b) Sakuda, S.; Yamada, Y. In Comprehensive Natural Products
Chemistry; Barton, D. H. R., Nakanishi, K., Meth-Cohn, O., Eds.; Pergamon: 1999;
For representative examples (see Scheme 1): (c) Goniobutenolides: Fang, X.;
Anderson, J. E.; Chang, C.; McLaughlin, J. L. Tetrahedron 1991, 47, 9751–9758; (d)
Fimbrolides: Kazlauskas, R.; Murphy, P. T.; Quinn, R. J.; Wells, R. J. Tetrahedron
Lett. 1977, 19, 37–40; (e) Nostoclides: Yang, X.; Shimizu, Y.; Steiner, J. R.; Clardy,
J. Tetrahedron Lett. 1993, 34, 761–764.
2. Baer, H.; Holden, M.; Seegal, B. C. J. Biol. Chem. 1946, 162, 65–68.
3. Song, P. S.; Koka, P.; Prezelin, B. B.; Haxo, F. T. Biochemistry 1976, 15, 4422–4427.
4. Konaklieva, M. I.; Plotkin, B. J. Mini-Rev. Med. Chem. 2005, 5, 73–95.
5. Kuhnt, D.; Anke, T.; Besl, H.; Bross, M.; Herrmann, R.; Mocek, U.; Steffan, B.;
Steglich, W. J. Antibiot. 1990, 43, 1413–1420.
6. Suga, H.; Smith, K. M. Curr. Opin. Microbiol. 2003, 7, 586–591.