9090
I. De´champs et al. / Tetrahedron 63 (2007) 9082–9091
The crude oil was purified by flash column chromatography
on silica gel (CHCl /MeOH: 90/10) to give 24 (58 mg,
0.23 mmol, 82% yield) as a yellow oil. The spectroscopic
data are in agreement with those described in literature.
11. (a) Cossy, J.; Dumas, C.; Michel, P.; Gomez Pardo, D.
Tetrahedron Lett. 1995, 36, 549; (b) Cossy, J.; Dumas, C.;
Gomez Pardo, D. Synlett 1997, 905; (c) Cossy, J.; Dumas, C.;
Gomez Pardo, D. Bioorg. Med. Chem. Lett. 1997, 7, 1343;
3
(
d) Wilken, J.; Kossenjans, M.; Saak, W.; Haase, D.; Pohl, S.;
2
0
25
20
[
C H )]. IR (film): 2931, 2886, 2857, 2778, 1467, 1368,
a] ꢀ88.9 (c 0.70, C H ) [lit.: [a]D ꢀ91.7 (c 0.955,
Martens, J. Liebigs Ann. 1997, 573; (e) Langlois, N.; Calvez,
O. Synth. Commun. 1998, 28, 4471; (f) Davis, P. W.; Osgood,
S. A.; H ꢀe bert, N.; Sprankle, K. G.; Swayze, E. E. Biotechnol.
Bioeng. 1999, 61, 143; (g) Cossy, J.; Dumas, C.; Gomez
Pardo, D. Eur. J. Org. Chem. 1999, 1693; (h) Michel, P.;
Rassat, A. J. Org. Chem. 2000, 65, 2572; (i) Cossy, J.;
Mirguet, O.; Gomez Pardo, D. Synlett 2001, 1575; (j) Brandi,
A.; Cicchi, S.; Paschetta, V.; Gomez Pardo, D.; Cossy, J.
Tetrahedron Lett. 2002, 43, 9357; (k) Deyine, A.; Delcroix,
J.-M.; Langlois, N. Heterocycles 2004, 64, 207; (l)
D ꢀe champs, I.; Gomez Pardo, D.; Karoyan, P.; Cossy, J.
Synlett 2005, 1170; (m) Roudeau, R.; Gomez Pardo, D.;
Cossy, J. Tetrahedron 2006, 62, 2388; (n) Mena, M.;
Bonjoch, J.; Gomez Pardo, D.; Cossy, J. J. Org. Chem. 2006,
D
6 6
6
6
ꢀ
1
1
1253, 1148, 1095 cm
d 0.05 (s, 3H), 0.07 (s, 3H), 0.99 (s, 9H), 1.27 (m, 1H),
.
H NMR (C D , 400 MHz):
6 6
1
4
(
.41 (m, 1H), 1.59 (m, 1H), 1.89 (ddd, J¼12.2, 7.9,
.0 Hz, 1H), 2.25 (ddd, J¼11.6, 11.6, 2.9 Hz, 1H), 2.72
dd, J¼11.2, 4.8 Hz, 1H), 3.04 (m, 1H), 3.13 (dddd,
J¼12.5, 6.5, 2.0, 2.0 Hz, 1H), 3.54 (dddd, J¼12.5, 3.9,
1
(
.9, 1.9 Hz, 1H), 3.60 (ddd, J¼10.2, 8.8, 4.4 Hz, 1H), 5.69
1
3
ddd, J¼6.2, 4.0, 2.1 Hz, 1H), 6.18 (m, 1H). C NMR
(
C D , 100 MHz): d ꢀ4.5 (q), ꢀ4.1 (q), 18.3 (s), 25.2 (t),
6
6
2
6.1 (q), 35.1 (t), 49.1 (t), 58.3 (t), 72.5 (d), 74.8 (d), 128.9
d), 131.5 (d). MS (CI, CH ) m/z (relative intensity): 254
(
4
+
(
MH , 100), 144 (3), 120 (24), 111 (3).
7
1, 5930.
1
1
2. (a) Calvez, O.; Chiaroni, A.; Langlois, N. Tetrahedron Lett.
1998, 39, 9447; (b) Cossy, J.; Mirguet, O.; Gomez Pardo, D.;
Desmurs, J.-R. Tetrahedron Lett. 2001, 42, 7805; (c) Cossy,
J.; Mirguet, O.; Gomez Pardo, D.; Desmurs, J.-R. Eur. J.
Org. Chem. 2002, 3543.
Acknowledgements
Johnson & Johnson is greatly acknowledged for financial
support (Focus Giving Program to J.C.).
3. (a) Hammer, C. F.; Heller, S. R.; Craig, J. H. Tetrahedron 1972,
8, 239; (b) Paul, R.; Tchelitcheff, S. Bull. Soc. Chim. Fr. 1958,
2
References and notes
736; (c) Kim, D.-K.; Kim, G.; Kim, Y.-W. J. Chem. Soc., Perkin
Trans. 1 1996, 803; (d) Lee, J.; Hoang, T.; Lewis, S.; Weissman,
S. A.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron Lett.
2001, 42, 6223; (e) Verhelst, S. H. L.; Martinez, B. P.; Timmer,
M. S. M.; Lodder, G.; Van der Marel, G. A.; Overkleeft, H. S.;
Van Boom, J. H. J. Org. Chem. 2003, 68, 9598.
1
2
3
4
. (a) Michael, J. P. Nat. Prod. Rep. 2001, 18, 520; (b) Michael,
J. P. Nat. Prod. Rep. 2000, 17, 579.
. Guengerich, F. P.; DiMari, S. J.; Broquist, H. P. J. Am. Chem.
Soc. 1973, 95, 2055.
. Liao, Y. F.; Lal, A.; Moremen, K. W. J. Biol. Chem. 1996, 271,
14. For reviews on metathesis applied to nitrogen containing sub-
strate, see: (a) Phillips, A. J.; Abell, A. D. Aldrichimica Acta
1999, 32, 75; (b) Vernall, A. J.; Abell, A. D. Aldrichimica
Acta 2003, 36, 93; (c) Felpin, F.-X.; Lebreton, J. Eur. J. Org.
Chem. 2003, 3693; (d) Deiters, A.; Martin, S. F. Chem. Rev.
2004, 104, 2199.
2
8348.
. (a) Elbein, A. D.; Solf, R.; Dorling, P. R.; Vosbeck, K. Proc.
Natl. Acad. Sci. U.S.A. 1981, 78, 7393; (b) Kaushal, G. P.;
Szumilo, T.; Pastuszak, I.; Elbein, A. D. Biochemistry 1990,
2
9, 2168; (c) Pastuszak, I.; Kaushal, G. P.; Wall, K. A.; Pan,
Y. T.; Sturm, A.; Elbein, A. D. Glycobiology 1990, 1, 71.
. (a) White, S. L.; Nagai, T.; Akiyama, S. K.; Reeves, E. J.;
Grzegorzewski, K.; Olden, K. Cancer Commun. 1991, 3, 83;
(b) Das, P. C.; Roberts, J. D.; White, S. L.; Olden, K. Oncol.
Res. 1995, 7, 425.
15. Bejjani, J.; Chemla, F.; Audouin, M. J. Org. Chem. 2003, 68,
9747.
16. (a) Lubell, W. D.; Rappoport, H. J. Am. Chem. Soc. 1987, 109,
236; (b) Rittle, K. E.; Homnick, C. F.; Ponticello, G.; Evans,
B. E. J. Org. Chem. 1982, 47, 3016.
5
6
. Klein, J. L.; Roberts, J. D.; George, M. D.; Kurtzberg, J.;
Breton, P.; Chermann, J. C. Br. J. Cancer 1999, 80, 87.
. (a) Mezher, H. A.; Hough, L.; Richardson, A. C. J. Chem. Soc.,
Chem. Commun. 1984, 447; (b) Fleet, G. W. J.; Gouh, M. J.;
Smith, P. W. Tetrahedron Lett. 1984, 25, 1853; (c) Suami, T.;
Tadano, K.; Iimura, Y. Chem. Lett. 1984, 513; (d) Adams,
C. E.; Walker, F. J.;Sharpless, K. B. J. Org. Chem. 1985, 50, 420.
. For review, see: (a) Nemr, A. E. Tetrahedron 2000, 56, 8579;
17. (a) Kiyooka, S.-I.; Nakano, M.; Shiota, F.; Fujiyama, R. J. Org.
Chem. 1989, 54, 5409; (b) Reed, P. E.; Ketzenellenbogen, J. A.
J. Org. Chem. 1991, 56, 2624; (c) St-Denis, Y.; Chan, T.-H. J.
Org. Chem. 1992, 57, 3078; (d) Barrett, A. G. M.; Damiani, F.
J. Org. Chem. 1999, 64, 1410; (e) Andr ꢁe s, J. M.; Pedrosa, R.;
P ꢀe rez, A.; P ꢀe rez-Encabo, A. Tetrahedron 2001, 57, 8521; (f)
Ma, D.; Pan, Q.; Han, F. Tetrahedron Lett. 2002, 43, 9401.
18. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999,
1, 953.
19. For recent examples of diastereoselective dihydroxylation on
these systems, see: (a) Duvold, T.; Rohmer, M. Tetrahedron
1999, 55, 9847; (b) Duvold, T.; Rohmer, M. Tetrahedron
Lett. 2000, 41, 3865; (c) Fazio, F.; Schneider, M. P.
Tetrahedron: Asymmetry 2001, 12, 2143; (d) Dehoux, C.;
Gorrichon, L.; Baltas, M. Eur. J. Org. Chem. 2001, 6, 1105.
20. (a) Shing, T. K. M.; Tai, V. W.-F.; Tam, E. K. W. Angew. Chem.,
Int. Ed. Engl. 1994, 33, 2312; (b) Shing, T. K. M.; Tam,
E. K. W.; Tai, V. W.-F.; Chung, I. H. F.; Jiang, Q. Chem.—
Eur. J. 1996, 2, 50; (c) Hegedus, L. S.; Geisler, L.; Riches,
7
8
9
(
. (a) Song, L.; Duesler, E. N.; Mariano, P. S. J. Org. Chem. 2004,
b) Pyne, S. G. Curr. Org. Synth. 2005, 2, 39.
6
9, 7284; (b) Heimg €a rtner, G.; Raatz, D.; Reiser, O. Tetrahedron
2
005, 61, 643; (c) Mart ꢀı n, R.; Murruzzu, C.; Peric ꢁa s, M. A.;
Riera, A. J. Org. Chem. 2005, 70, 2325; (d) Guo, H.;
O’Doherty, G. A. Org. Lett. 2006, 8, 1609; (e) Au, C. W. G.;
Pyne, S. G. J. Org. Chem. 2006, 71, 7097; (f) Ceccon, J.;
Greene, A. E.; Poisson, J.-F. Org. Lett. 2006, 8, 4739.
1
0. For comprehensive reviews, see: (a) Cossy, J.; Gomez Pardo,
D. Chemtracts 2002, 15, 579; (b) Cossy, J.; Gomez Pardo, D.
Targets Heterocycl. Syst. 2002, 6, 1.