1464
M. Deligny et al.
LETTER
(14) The absolute configuration of the four stereocenters was
confirmed by the examination of its X-ray crystal structure.
See ref. 11b.
(15) At this temperature, we observed a slow transformation of
aldehyde 4 into benzaldehyde.
(16) The stereoselectivity of 7 has been studied with various
chiral aldehydes. These results will be reported elsewhere.
(17) Grieco, P. A.; Oguri, T.; Yokoyama, Y. Tetrahedron Lett.
1978, 19, 419.
(18) Génisson, Y.; Tyler, P. C.; Young, R. N. J. Am. Chem. Soc.
1994, 116, 759.
availability of both isomers of mandelic acid and chromi-
um(III) complex, makes this procedure especially attrac-
tive for the synthesis of stereoisomers of (+)-goniodiol.
Application of this methodology to the preparation of
other natural styryllactones is currently underway at the
laboratory.
Acknowledgment
M. Deligny thanks the Ministère de l’Education Nationale, de la
Recherche et de la Technologie (MENRT) for a PhD grant. The
CNRS and the University of Rennes 1 are gratefully acknowledged
for financial support of this research.
(19) Ogawa, T.; Katano, K.; Matsui, M. Tetrahedron 1980, 36,
2727.
(20) All new compounds were fully characterized (1H NMR, 13
NMR, elemental analysis or HRMS).
C
Compound 9: [a]D20 –145.9 (c 1.11, CHCl3). 1H NMR (300
MHz, CDCl3): d = 1.20 (t, 3 H, J = 7.1 Hz), 2.12 (m, 2 H),
3.33 (dq, 1 H, J = 7.1, 9.5 Hz), 3.80 (dq, 1 H, J = 7.1, 9.0
Hz), 4.09 (m, 1 H), 4.40 (dd, 1 H, J = 3.6, 7.4 Hz), 4.92 (dd,
1 H, J = 3.8, 7.8 Hz), 5.34 (m, 1 H), 5.79 (m, 1 H), 5.82 (d,
1 H, J = 7.8 Hz), 7.32 (m, 5 H). 13C NMR (75 MHz, CDCl3):
d = 15.2, 30.5, 64.2, 71.8, 79.7, 80.8, 98.0, 123.5, 127.2,
126.3, 128.5, 129.1, 132.9, 154.5. Anal. Calcd for C16H18O5:
C, 66.20; H, 6.25. Found: C, 66.22; H, 6.33.
References
(1) Wu, Y.-C.; Duh, C.-Y.; Chang, F.-R.; Chang, G.-Y.; Wang,
S.-K.; Chang, J.-J.; McPhail, D. R.; McPhail, A. T.; Lee, K.-
H. J. Nat. Prod. 1991, 54, 1077.
(2) Fang, X.-P.; Anderson, J. E.; Smith, D. L.; McLaughlin, J.
L.; Wood, K. V. J. Nat. Prod. 1992, 55, 1655; and references
cited therein.
(3) Lu, S.-T.; Wu, Y.-C.; Leou, S.-P. Phytochemistry 1985, 24,
1829.
(4) Fang, X.-P.; Anderson, J. E.; Chang, C.-J.; McLaughlin, J.
L.; Fanwick, P. E. J. Nat. Prod. 1991, 54, 1034; and
references cited therein.
(5) Blasquez, M. A.; Bermejo, A.; Zafra-Polo, M. C.; Cortes, D.
Phytochem. Anal. 1999, 10, 161.
(6) Talapatra, S. K.; Basu, D.; Deb, T.; Goswami, S.; Talapatra,
B. J. Indian Chem. Soc. 1985, 24B, 29.
(7) Mu, Q.; Tang, W.; Li, C.; Lu, Y.; Sun, H.; Zheng, H.; Hao,
X.; Zheng, Q.; Wu, N.; Lou, L.; Xu, B. Heterocycles 1999,
51, 2969.
(8) Lan, Y.-H.; Chang, F.-R.; Yu, J.-H.; Yang, Y.-L.; Chang, Y.-
L.; Lee, S.-J.; Wu, Y.-C. J. Nat. Prod. 2003, 66, 487.
(9) (a) Mukai, C.; Hirai, S.; Hanaoka, M. J. Org. Chem. 1997,
62, 6619. (b) Dixon, D. J.; Ley, S. V.; Tate, E. W. J. Chem.
Soc., Perkin Trans. 1 1998, 3125. (c)Survivet, J.-P.;Vatèle,
J.-M. Tetrahedron 1999, 55, 13011. (d) Tsubuki, M.; Kanai,
K.; Nagase, H.; Honda, T. Tetrahedron 1999, 55, 2493.
(10) (a) Survivet, J.-P.; Goré, J.; Vatèle, J.-M. Tetrahedron 1996,
52, 14877. (b) Banwell, M. G.; Coster, M. J.; Karunaratne,
O. P.; Smith, J. A. J. Chem. Soc., Perkin Trans. 1 2002,
1622. (c) Chen, J.; Lin, G.-Q.; Wang, Z.-M.; Liu, H.-Q.
Synlett 2002, 1265. (d) Ramachandran, P. V.; Chandra, J. S.;
Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547.
(11) (a) Deligny, M.; Carreaux, F.; Carboni, B.; Toupet, L.;
Dujardin, G. Chem. Commun. 2003, 276. (b) Deligny, M.;
Carreaux, F.; Toupet, L.; Carboni, B. Adv. Synth. Catal.
2003, 345, 1215. (c) Gao, X.; Hall, D. G. J. Am. Chem. Soc.
2003, 125, 9308.
Compound 11: [a]D20 –144.3 (c 0.62, CH2Cl2). 1H NMR
(300 MHz, CDCl3): d = 2.22 (m, 1 H), 2.70 (m, 1 H), 4.15
(ddd, 1 H, J = 1.1, 3.8, 12.8 Hz), 4.98 (dd, 1 H, J = 1.1, 8.1
Hz), 5.87 (dd, 1 H, J = 2.3, 9.9 Hz), 5.98 (d, 1 H, J = 8.1 Hz),
6.85 (ddd, 1 H, J = 2.1, 6.4, 9.9 Hz), 7.48 (m, 5 H). 13C NMR
(75 MHz, CDCl3): d = 29.6, 72.8, 78.0, 79.2, 119.7, 123.7,
125.3, 127.7, 128.4, 130.4, 153.0, 160.8. Anal. Calcd for
C14H12O5: C, 64.61; H, 4.65. Found: C, 64.46; H, 4.60.
Compound 12: [a]D20 +64.1 (c 0.32, CH2Cl2). 1H NMR (300
MHz, CDCl3): d = 1.02 (s, 9 H), 1.18 (t, 3 H, J = 7.1 Hz),
2.05–2.30 (m, 2 H), 3.22 (dq, 1 H, J = 7.1, 9.5 Hz), 3.70 (m,
1 H), 4.23 (d, 1 H, J = 11.1 Hz), 4.35 (d, 1 H, J = 11.1 Hz),
4.44 (dd, 1 H, J = 3.2, 8.4 Hz), 4.67 (m, 1 H), 5.02 (d, 1 H,
J = 6.7 Hz), 5.52 (dd, 1 H, J = 1.2, 9.8 Hz), 7.00–7.55 (m, 16
H), 7.67 (m, 2 H), 7.76 (m, 2 H). 13C NMR (75 MHz,
CDCl3): d = 15.1, 19.4, 26.9, 27.1, 31.4, 63.7, 74.4, 74.6,
75.1, 85.0, 98.7, 124.4, 127.2, 127.3, 127.4, 127.5, 127.7,
127.9, 128.1, 128.6, 129.4, 129.5, 129.6, 133.4, 134.0,
134.8, 136.0, 136.1, 138.6, 141.2. HRMS (ES): m/z calcd for
C38H44O4Si [M + Na]+: 615.2907; found: 615.2902.
Compound 13: [a]D20 +45.9 (c 1.82, CH2Cl2). 1H NMR (300
MHz, CDCl3): d = 1.06 (s, 9 H), 2.00 (ddd, 1 H, J = 3.7, 6.2,
18.1 Hz), 2.42 (m, 1 H), 3.58 (dd, 1 H, J = 2.5, 7.8 Hz), 3.90
(d, 1 H, J = 18.4 Hz), 3.95 (d, 1 H, J = 18.4 Hz), 4.76 (td, 1
H, J = 3.0, 12.6 Hz), 5.11 (d, 1 H, J = 7.8 Hz), 5.89 (dd, 1 H,
J = 2.4, 9.8 Hz), 6.75 (ddd, 1 H, J = 2.1, 6.2, 9.8 Hz), 7.01
(m, 2 H), 7.19–7.68 (m, 18 H). 13C NMR (75 MHz, CDCl3):
d = 19.4, 26.1, 27.1, 74.1, 74.5, 76.3, 83.9, 121.1, 127.3,
127.5, 127.6, 127.7, 127.8, 127.9, 128.0, 128.1, 128.2,
129.5, 129.7, 133.1, 133.5, 135.9, 136.0, 137.6, 141.3,
144.8, 163.5. HRMS (ES): m/z calcd for C36H38O4Si [M +
Na]+: 585.2437; found: 585.2434.
(12) Rasset-Deloge, C.; Martinez-Fresneda, P.; Vaultier, M. Bull.
Soc. Chim. Fr. 1992, 129, 285.
(13) Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Angew.
Chem. Int. Ed. 2002, 41, 3059.
Synlett 2005, No. 9, 1462–1464 © Thieme Stuttgart · New York