4740
A. Valla et al. / Tetrahedron Letters 44 (2003) 4737–4740
14. Corey, E. J.; Fraenkel, G. J. Am. Chem. Soc. 1953, 75,
Acknowledgements
1168–1172.
We are indebted to Professor G. Ourisson for helpful
discussions.
15. Standard procedure: After treating of 10 mmol of diacid
(see tables), the solvent was removed in vacuo and the
oily mixture was extracted with Et2O. The acids 3, 4
and 5 were extracted with a saturated NaHCO3 solu-
tion. The neutral organic layer, constituted of com-
pounds 2 and 6 was washed with water, dried over
MgSO4 and the solvent removed in vacuo. Purification
by chromatography on silica gel, using dichloromethane
as eluent, yielded the decarboxylated compound 2 or the
lactone 6.
References
1. (a) Biswas, M. K.; Majumdar, D. K. J. Indian Chem.
Soc. 1981, 58, 868–870; (b) Haleem, M. A. Collect.
Czech. Chem. Commun. 1970, 35, 2854–2857; (c)
Gopalan, R.; Mathai, I. M. Proc. Indian Acad. Sci.,
Sect. A 1969, 70, 92–98; (d) Clark, L. W. J. Phys. Chem.
1969, 73, 438–442.
2a: colourless oil. 1H NMR (400 MHz, CDCl3): 6.44
(dd, 1H, J=15.3, J=10.8, H4); 6.26 (d, 1H, J=10.8,
H5); 5.12 (m, 1H, H9); 4.97 (m, 2H, H1a+H1b); 2.13 (s,
4H, 7-CH2 and 8-CH2); 1.92 (s, 3H, 6-CH3); 1.82 (s, 3H,
2-CH3); 1.71 (s, 3H, 10b-CH3); 1.63 (s, 3H, 10a-CH3).
13C NMR (CH): 133.6, C3; 126.0, C4; 124.3, C5; 122.2,
2. Toussaint, O.; Capdevielle, P.; Maumy, M. Synthesis
1986, 1029–1031.
3. Mura, K.; Tada, M. Waseda Daigaku Rikogaku
Kenkyusho Hokoku 1978, 80, 68–69.
4. (a) Haleem, M. A.; Chenite, A. Muslim. Sci. 1982, 11,
577–581; (b) Cavalleri, B.; Bellasio, E.; Vigevani, A.;
Testa, E. Farmaco Ed. Sci. 1969, 24, 451–470; (c)
Biswas, M. K.; Majumdar, D. K. Bull. Soc. Chem. Jpn.
1981, 54, 2213–2214.
5. Clark, L. W. J. Phys. Chem. 1967, 71, 2597–2601.
6. Lynn, Z.; Cynthia, J.; Giguere, R. J. Synth. Commun.
2000, 30, 2099–2104.
C9 (CH2): 115.9, C1; 40,5, C7; 27.0, C8 (CH3) 26.1, C10b
19.0, C2; 18.1, C10a; 17.2, C6.
;
2b: colourless oil. 1H NMR (400 MHz, CDCl3): 6.59
(dd, 1H, J=15.2, J=11.3, H4); 6.36 (d, 1H, J=15.2,
H3); 6.15 (2d, 2H, J=15.2, H8, J=11.3, H5); 6.13 (d,
1H, J=15.2, H7); 5.02 and 5.00 (2s, H1a+H1b). 13C
NMR (CH): 138.1, C7; 135.5, C3; 130.4, C5; 127.1, C10;
126.1, C4; (CH2): 116.8, C1; 40.0, C13; 33.5, C11; 19.7,
C12 (CH3) 29.4, C14; 22.1, C10; 19.1, C2; 13.1, C6.
7. Brunner, H.; Mueller, J.; Spitzer, J. Monatsch. Chem.
1996, 127, 845–858.
1
5c: colourless oil. H NMR (400 MHz, CDCl3): 7.30 (m,
8. Valla, A.; Andriamialisoa, Z.; Giraud, M.; Prat, V.;
Laurent, A.; Labia, R.; Potier, P. Tetrahedron Lett.
1999, 40, 9235–9237.
9. Valla, A.; Andriamialisoa, Z.; Giraud, M.; Prat, V.;
Laurent, A.; Labia, R.; Potier, P. Tetrahedron 2000, 56,
7211–7215.
10. (a) Liebermann, C.; Riiber, C. N. Chem. Ber. 1902, 35,
2696; (b) Riiber, C. Chem. Ber. 1904, 37, 2274.
11. Oda, N.; Yoshida, Y.; Nagai, S.; Ueda, T.; Sakakibara,
J. Chem. Pharm. Bull. 1987, 35, 1796–1802.
12. Rodionow, V. M.; Veselovskaya, T. K. Zhur. Obshchei
Khim. 1950, 20, 2202–2212 (engl. Ausg. 2287–2295).
13. Giraud, M.; Molho, D. Bull. Soc. Chim. Fr. 1970, 2651–
2656.
5H, Ar); 5.46 (d, 1H, J=12.3, H7); 3.04 (dd, 1H, J=
18.9, J=12.3, H8); 2.82 (d, 1H, J=18.9, H8%); 2.58 (s,
3H, 9-CH3).
1
5d: colourless oil. H NMR (CDCl3): 7.29 (m, 5H, Ar);
5.90 (s, 1H, H10); 5.40 (dd, 1H, J=12.0, J=4.0, H7);
2.64 (dd, 1H, J=17.9, J=12.0, H8); 2.45 (dd, 1H, J=
17.9 J=4.0, H8%); 2.02 5s, 3H, 9-CH3).
1
6d: colourless oil. H NMR (400 MHz, CDCl3): 7.31 (m,
5H, Ar); 6.73 (d, 1H, J=16.0, H7); 6.27 (dd, 1H, J=
16.0, J=6.2, H8); 5.87 (s, 1H, H12); 5.06 (m, 1H, J=
10.7, J=5.6, J=5.2, H9); 2.52 (dd, 1H, J=17.8,
J=10.7, H10); 2.14 (dd, 1H, J=17.8, J=4.2, H10%); 2.02
(s, 3H, 11-CH3).