886
T. Hattori et al. / Tetrahedron: Asymmetry 15 (2004) 881–887
4.9.3.
Di[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]
References and notes
(Sa,Ra)-2,200-dimethoxy-1,10:40,100-ternaphthalene-20,30-di-
21
D
1. Review: (a) Rosini, C.; Franzini, L.; Raffaelli, A.; Salva-
dori, P. Synthesis 1992, 503; (b) Pu, L. Chem. Rev. 1998,
98, 2405.
2. (a) Yamamoto, K.; Yumioka, H.; Okamoto, Y.; Chik-
amatsu, H. J. Chem. Soc., Chem. Commun. 1987, 168; (b)
carboxylate cis-4. As crystals, mp 233–235 ꢁC; ½aꢁ ¼
)65.6 (c 1.02, CHCl3) (Found: C, 80.54; H, 7.53. Calcd
for C54H60O6: C, 80.56; H, 7.51); mmax (KBr)/cmꢂ1 1710;
dH (400 MHz) 0.25–1.57 (36H, m, menthyl), 3.78 (3H, s,
OMe), 3.88 (3H, s, OMe), 4.30 (1H, td, J 10.8 and 4.3,
OCH), 4.39 (1H, td, J 10.7 and 4.2, OCH), 7.12–7.39
(10H, m, ArH), 7.40 (1H, d, J 9.0, ArH), 7.46 (1H, d, J
9.0, ArH), 7.83–7.89 (2H, m, ArH) and 7.99 (2H, d, J
9.0, ArH).
€
Muller, U.; Baumgarten, M. J. Am. Chem. Soc. 1995, 117,
5840; (c) Pu, L. Chem. Eur. J. 1999, 5, 2227; (d) Fuji, K.;
Furuta, T.; Otsubo, T.; Tanaka, K. Tetrahedron Lett.
1999, 40, 3001; (e) Ma, L.; White, P. S.; Lin, W. J. Org.
Chem. 2002, 67, 7577; (f) Tsubaki, K.; Tanaka, H.;
Furuta, T.; Tanaka, K.; Kinoshita, T.; Fuji, K. Tetra-
hedron 2002, 58, 5611.
4.10. (Sa,Sa)-20,30-Dihydroxymethyl-2,200-dimethoxy-
1,10:40,100-ternaphthalene (Sa,Sa)-15
3. (a) Hayashi, T.; Hayashizaki, K.; Ito, Y. Tetrahedron Lett.
1989, 30, 215; (b) Marin, G. H.; Horak, V. J. Org. Chem.
ꢀ
ꢁ
1994, 59, 4267; (c) Belohradsky, M.; Budesınsky, M.;
Gunterova, J.; Hodacova, J.; Holy, P.; Zavada, J.;
ꢀꢀꢁ
ꢁ
€
ꢁ
ꢀ
ꢁ
ꢁ
ꢁ
To a solution of ternaphthalene (Sa,Sa)-4 (45.1 mg,
56.0 lmol) in dry THF (3.0 cm3) was added LiAlH4
(22.5 mg, 593 lmol) and the mixture stirred at room
temperature for 3 h. The mixture was cooled in an ice
bath and quenched by the successive addition of water
and 2 M HCl. The mixture was extracted with diethyl
ether and the extract washed with brine, dried over
Na2SO4 and evaporated. The residue was chromato-
graphed on silica gel with hexane–ethyl acetate (1:2) as
the eluent to give diol (Sa2,5Sa)-15 (25.4 mg, 91%) as
ꢁ ꢀ
ꢁ
Cısarova, I.; Podlaha, J. J. Org. Chem. 1996, 61, 1205;
(d) Hagen, S.; Scott, L. T. J. Org. Chem. 1996, 61, 7198;
(e) Zoltewicz, J. A.; Maier, N. M.; Lavieri, S.; Ghiviriga,
I.; Abboud, K. A.; Fabian, W. M. F. Tetrahedron 1997,
53, 5379; (f) Harada, N.; Hiyoshi, N.; Vassilev, V. P.;
Hayashi, T. Chirality 1997, 9, 623; (g) Bringmann, G.;
Wuzik, A.; Kraus, J.; Peters, K.; Peters, E.-M. Tetrahe-
dron Lett. 1998, 39, 1545; (h) Sugimura, T.; Inoue, S.; Tai,
A. Tetrahedron Lett. 1998, 39, 6487; (i) Fuji, K.; Furuta,
T.; Tanaka, K. Org. Lett. 2001, 3, 169; (j) Chow, H.-F.;
Wan, C.-W. J. Org. Chem. 2001, 66, 5042; (k) Habaue, S.;
Seko, T.; Okamoto, Y. Macromolecules 2002, 35, 2437.
4. (a) Miyano, S.; Okada, S.; Hotta, H.; Takeda, M.;
Kabuto, C.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1989,
62, 1528; (b) Miyano, S.; Okada, S.; Hotta, H.; Takeda,
M.; Suzuki, T.; Kabuto, C.; Yasuhara, F. Bull. Chem. Soc.
Jpn. 1989, 62, 3886; (c) Goto, J.; Shao, G.; Fukasawa, M.;
Nambara, T.; Miyano, S. Anal. Sci. 1991, 7, 645; (d)
Fukushi, Y.; Yajima, C.; Mizutani, J. Tetrahedron Lett.
1994, 35, 599; (e) Latypov, S. K.; Aganov, A. V.; Tahara,
S.; Fukushi, Y. Tetrahedron 1999, 55, 7305; (f) Oi, S.;
Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue,
Y. J. Org. Chem. 1999, 64, 8660; (g) Hattori, T.; Minato,
Y.; Yao, S.; Finn, M. G.; Miyano, S. Tetrahedron Lett.
2001, 42, 8015; (h) Koshiishi, E.; Hattori, T.; Ichihara, N.;
Miyano, S. J. Chem. Soc., Perkin Trans. 1 2002, 377.
5. (a) Hattori, T.; Shijo, M.; Sakamoto, J.; Kumagai, S.;
Nakajima, A.; Miyano, S. J. Chem. Res. (M) 1995, 124;
(b) Ito, Y.; Miyake, T.; Hatano, S.; Shima, R.; Ohara, T.;
Suginome, M. J. Am. Chem. Soc. 1998, 120, 11880; (c)
Fukui, H.; Fukushi, Y.; Tahara, S. Tetrahedron Lett.
1999, 40, 325; (d) Murase, N.; Hoshino, Y.; Oishi, M.;
Yamamoto, H. J. Org. Chem. 1999, 64, 338; (e) Einhorn,
C.; Einhorn, J.; Marcadal-Abbadi, C.; Pierre, J.-L. J. Org.
Chem. 1999, 64, 4542; (f) Hungerhoff, B.; Metz, P.
crystals, mp 308–310 ꢁC; ½aꢁ ¼ +16.9 (c 0.40, CHCl3)
D
(Found: C, 81.54; H, 5.70. Calcd for C34H28O4: C, 81.58;
H, 5.64); mmax (KBr)/cmꢂ1 3370; dH (400 MHz) 3.85 (6H,
s, 2 · OMe), 4.57 (2H, d, J 12.0, 2 · CH), 4.73 (2H, d, J
12.0, 2 · CH), 7.15–7.21 (6H, m, ArH), 7.27–7.31 (2H,
m, ArH), 7.36–7.40 (2H, m, ArH), 7.53 (2H, d, J 8.0,
ArH), 7.92 (2H, d, J 9.1, ArH) and 8.06 (2H, d, J 8.9,
ArH).
4.11. Reaction of dimenthyl ester 11 with Grignard
reagent 12
This reaction was performed in diethyl ether–benzene by
the same procedure used for the reaction between ester
10 and Grignard reagent 12. Column chromatography
isolated the following compound besides isomers cis-4
and (Sa,Sa)-4.
4.11.1. Di[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]
(Ra,Ra)-2,200-dimethoxy-1,10:40,100-ternaphthalene-20,30-di-
carboxylate (Ra,Ra)-4. As an amorphous solid (Found:
C, 80.33; H, 7.80. Calcd for C54H60O6: C, 80.56; H,
7.51); dH (400 MHz) 0.46–1.68 (36H, m, menthyl), 3.81
(6H, s, 2 · OMe), 4.33–4.40 (2H, m, 2 · OCH) and 7.24–
8.00 (16H, m, ArH).
€
Tetrahedron 1999, 55, 14941; (g) Knolker, H.-J. Chem.
Rev. 2000, 100, 2941; (h) Brunner, H.; Henning, F.;
Weber, M. Tetrahedron: Asymmetry 2002, 13, 37; (i) Van
Veldhuizen, J. J.; Garber, S. B.; Kingsbury, J. S.;
Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 4954.
6. (a) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull.
Chem. Soc. Jpn. 1993, 66, 613; (b) Hattori, T.; Suzuki, T.;
Hayashizaka, N.; Koike, N.; Miyano, S. Bull. Chem. Soc.
Jpn. 1993, 66, 3034; (c) Hattori, T.; Koike, N.; Miyano, S.
J. Chem. Soc., Perkin Trans. 1 1994, 2273; (d) Hattori, T.;
Tanaka, H.; Okaishi, Y.; Miyano, S. J. Chem. Soc., Perkin
Trans. 1 1995, 235; (e) Hattori, T.; Hayashizaka, N.;
Miyano, S. Synthesis 1995, 41; (f) Hattori, T.; Koike, N.;
Okaishi, Y.; Miyano, S. Tetrahedron Lett. 1996, 37, 2057;
(g) Hattori, T.; Koshiishi, E.; Wada, S.; Koike, N.;
Yamabe, O.; Miyano, S. Chirality 1998, 10, 619; (h)
Acknowledgements
We are grateful to Dr. Osamu Yamabe for experimental
support. This study was supported in part by a grant
from the General Sekiyu Research Promotion Founda-
tion.