802
A. Wada et al.
LETTER
Table 2 Yields of Reactions for the Synthesis of 13-Substituted Retinoic Acids
a) Yield in 2 steps.
(6) Several similar cross coupling reactions for the stereoselective
synthesis of retinoids have already been reported; for all-E-
retinoids, a) Torrado, A.; Iglesias, B.; López, S.; de Lera, A.
R. Tetrahedron, 1995, 51, 2435; b) Torrado, A.; López, S.;
Alvarez, R.; de Lera, A. R. Synthesis, 1995, 285; c) Thibonnet,
J.; Abarbri, M.; Duchêne, A.;Parrain, J.-L. Synlett, 1999, 141;
d) Dominguez, B.; Iglesias, B.; de Lera, A. R. J. Org. Chem.,
1988, 63, 4135; For 9Z-retinoic acid, e) Pazos, Y.; de Lera, A.
R. Tetrahedron Lett., 1999, 40, 8287; For 11Z-retinal,
f) Uenishi, J.; Kawahama, R.; Yonemitsu, O.; Wada, A.; Ito,
M. Angew. Chem. Int. Ed., 1998, 37, 320.
Acknowledgement
This work was supported in part by a Grant-in-Aid for Scientific
Research (No. 12672165) from Ministry of Education, Science and
Culture, a Kobe Pharmaceutical University Collaboration Fund and
The Science Research Promotion Fund from Japan Private School
Promotion Foundation.
References and Notes
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MHz, CDCl3) 0.8-1.6 (31H, m), 0.89 (6H, s), 1.70 (3H, s),
1.95 (3H, s), 2.02 (2H, t, J = 7 Hz), 6.05 (1H, d, J = 16 Hz),
6.06 (1H, J = 11 Hz), 6.17 (1H, d, J = 16 Hz), 6.29 (1H, d,
J = 18 Hz), 6.92 (1H, dd, J = 18,11 Hz).
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(12) We found that this catalyst system is more effective than
tetrakistriphenylphosphine palladium(0) for the coupling
reaction of vinyl stannane with vinyl triflate, see ref. 5.
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(14) The yields of this reactions (2 steps) are as follows; 10b
(49%), 10c (34%), 10d (32%), 10e (33%).
(15) For preparation of 13-substituted all-E- retinal; Danshina, S.
V.; Drachev, A. L.; Drachev, L. A.; Eremin, S. V.; Kaulen, A.
D.; Khitrina, L. V.; Mitsner, B. I. Arc. Biochem. Biophys.,
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(4) a) Wada, A.; Hiraishi, S.; Ito, M. Chem. Pharm. Bull., 1994,
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Article Identifier:
1437-2096,E;2001,0,06,0800,0802,ftx,en;Y06901ST.pdf
(5) Wada, A.; Nomoto, Y.; Tano, K.; Yamashita, E.; Ito, M.
Chem. Pharm. Bull., 2000, 48, 1391.
Synlett 2001, No. 6, 800–802 ISSN 0936-5214 © Thieme Stuttgart · New York