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3263
Asymmetry 2001, 12, 2323–2329; (e) Fang, T.; Xu, J.-X.; Du, D.-M.
Synlett 2006, 1559–1563; (f) El Sheikh, S.; Kausch, N.; Lex, J.;
Neud o¨ rfl, J. M.; Schmalz, H. G. Synlett 2006, 1527–1530; (g) Yoon,
N. M.; Pak, C. S.; Brown, H. C.; Krishnamurthy, S.; Stochy, T. P. J.
Org. Chem. 1973, 38, 2786–2792; (h) Lobben, P. C.; Leung, S. S.-W.;
Tummala, S. Org. Process. Res. Dev. 2004, 8, 1072–1075; (i) Gibson,
S. E.; Mainolfi, N.; Kalindjian, S. B.; Wright, P. T.; White, A. J. P.
Chem. Eur. J. 2005, 11, 69–80; (j) Chen, M. H.; Iakovleva, E.; Kesten,
S.; Magano, J.; Rodriguez, D.; Sexton, K. E.; Zhang, J.; Lee, H. T.
Org. Prep. Proced. Int. 2002, 34, 665–670; (k) Stepanenko, V.; Jes u´ s,
M. D.; Correa, W.; Guzm a´ n, I.; V a´ zquez, C.; Cruz, W.; Ortiz-
Marciales, M.; Barnes, C. L. Tetrahedron Lett. 2007, 48, 5799–
which was washed with saturated aqueous sodium bicarbonate
(3 Â 10 mL) and brine (3 Â 10 mL). The organic layer was then dried
over anhydrous sodium sulfate, filtered, and concentrated to give
products.
15. Spectroscopic data for products:
1
Compound 1: H NMR (400 MHz, DMSO): d = 9.25 (s, 1H, Ph–
OH), 7.10 (d, J = 8.4 Hz, 2H, Ph–H), 6.70 (d, J = 8.4 Hz, 2H, Ph-H),
4.97 (t, J = 5.6 Hz, 1H, C–OH), 4.36 (d, J = 5.6 Hz, 2H, Ph–CH
2
).
): d = 7.35 (s, 1H, Ph–OH),
7.20 (t, J = 8.0 Hz, 1H, Ph–H), 7.03 (d, J = 7.6 Hz, 1H, Ph–H), 6.82–
6.90 (m, 2H, Ph–H), 4.83 (s, 2H, Ph–CH ), 2.53 (s, 1H, CH –OH).
1
Compound 2: H NMR (400 MHz, CDCl
3
2
2
1
Compound 3: H NMR (400 MHz, DMSO): d = 10.05 (s, 1H, Ph–
OH), 7.41 (d, J = 1.6 Hz, 1H, Ph–H), 7.10 (dd, J = 1.6, 8.0 Hz, 1H,
Ph–H), 6.90 (d, J = 8.0 Hz, 1H, Ph–H), 5.0 (br, 1H, C–OH), 4.37 (s,
5
802.
. (a) Chu, Y. B.; Shan, Z. X.; Liu, D. J.; Sun, N. N. J. Org. Chem. 2006,
1, 3998–4001; (b) Itsuno, S.; Matsumoto, T.; Sato, D.; Inoue, T. J.
4
5
7
2
2H, Ph–CH ).
1
Org. Chem. 2000, 65, 5879–5881.
Compound 4: H NMR (400 MHz, DMSO): d = 8.74 (s, 1H, Ph–
OH), 6.88 (s, 1H, Ph–H), 6.70 (br, 2H, Ph–H), 4.97 (t, J = 6.0 Hz, 1H,
. (a) Peuralahti, J.; Meri o¨ , L.; Mukkala, V.-M.; Blomberg, K.;
Hovinen, J. Bioorg. Med. Chem. Lett. 2006, 16, 4760–4762; (b)
Cesarini, S.; Colombo, N.; Pulici, M.; Felder, E. R.; Brill, W. K.-D.
Tetrahedron 2006, 62, 10223–10226; (c) Verniest, G.; Claessens, S.;
Kimpe, N. D. Tetrahedron Lett. 2006, 47, 3299–3302.
2 3
C–OH), 4.37 (d, J = 6.0 Hz, 2H, Ph–CH ), 3.75 (s, 3H, Ph–OCH ).
1
Compound 5: H NMR (400 MHz, DMSO): d = 9.25 (s, 1H, Ph–
OH), 7.09 (d, J = 8.0 Hz, 1H, Ph–H), 6.74 (br, 1H, Ph–H), 6.71 (d,
J = 8.0 Hz, 1H, Ph–H), 6.61 (dd, J = 1.6, 8.0 Hz, 1H, Ph–H), 4.8 (br,
6
7
8
. Atkins, W. J.; Burkhardt, E. R.; Matos, K. Org. Process. Res. Dev.
2
1H, C–OH), 4.41 (s, 2H, Ph–CH ).
Compound 6: H NMR (400 MHz, DMSO): d = 9.05 (s, 2H, Ph–
OH), 6.17 (s, 2H, Ph–H), 6.05 (s, 1H, Ph–H), 4.98 (t, J = 6.0 Hz, 1H,
1
2
006, 10, 1292–1295.
. Periasamy, M.; Thirumalaikumar, M. J. Organomet. Chem. 2000,
09, 137–151.
. (a) Ginnis, A.; Sandhoff, K. Angew. Chem., Int. Ed. Engl. 1989, 28,
6
CH
Compound 7: H NMR (400 MHz, CDCl
2
–OH), 4.30 (d, J = 6.0 Hz, 2H, Ph–CH
2
).
+ DMSO): d = 6.99 (d,
1
3
2
1
18–220; (b) Jiang, B.; Feng, Y.; Zheng, J. Tetrahedron Lett. 2000, 41,
0281–10283.
J = 8.4 Hz, 2H, Ph–H), 6.74 (d, J = 8.4 Hz, 2H, Ph–H), 3.60 (t,
J = 6.8 Hz, 2H, HO–CH ), 2.58 (t, J = 8.0 Hz, 2H, Ph–CH ), 1.81 (m,
2H, Ph–C–CH ).
Compound 8: H NMR (400 MHz, DMSO): d = 9.10 (s, 1H, Ph–
OH), 6.99 (d, J = 8.4 Hz, 2H, Ph–H), 6.66 (d, J = 8.4 Hz, 2H, Ph–H),
2
2
9
. Kanth, J. V. B.; Periasamy, M. J. Org. Chem. 1991, 56, 5964–5965.
0. Suseela, Y.; Periasamy, M. Tetrahedron 1992, 48, 371–376.
1. Tale, R. H.; Patil, K. M.; Dapurkar, S. E. Tetrahedron Lett. 2003, 44,
2
1
1
1
3
427–3428.
2. (a) Narasimhan, S.; Madhavan, S.; Prasad, K. G. J. Org. Chem. 1995,
0, 5314–5315; (b) Berkes, D.; Kolarovic, A.; Povazanec, F. Tetra-
4.55 (t, J = 4.8 Hz, 1H, C–OH), 3.53 (m, 2H, HO–CH
J = 7.2 Hz,2H, Ph–CH ).
Compound 9: H NMR (400 MHz, CDCl
7.28 (s, 1H, Ph–H), 6.89 (s, 1H, Ph–H), 4.82 (s, 2H, Ph–CH
2
), 2.60 (t,
1
2
1
6
3
): d = 7.54 (s, 1H, Ph–OH),
), 2.2 (br,
hedron Lett. 2000, 41, 5257–5260; (c) Liu, C.; Burnell, J. Tetrahedron
Lett. 1997, 38, 6573–6576.
2
t
t
1H, C–OH), 1.43 (s, 9H, Ph– Bu), 1.28 (s, 9H, Ph– Bu).
1
1
3. (a) Unangst, P. U.; Connor, D. T.; Cetenko, W. A.; Sorenson, R. J.;
Kostlan, C. R.; Sircar, J. C.; Wright, C. D.; Schrier, D. J.; Dyer, R. D.
J. Med. Chem. 1994, 37, 322–328; (b) Martin, L.; Rabasseda, X.;
Castaner, J. Drug Future 1999, 24, 853–857; (c) Lin, J.; Lin, Z.; Feng,
Y. CN 1 858 041, 2006. Chem. Abstr. 2006, 146, 7947.
Compound 10: H NMR (400 MHz, DMSO): d = 9.83 (s, 1H, Ph–
OH), 7.28 (d, J = 8.0 Hz, 1H, Ph–H), 6.83 (dd, J = 2.0, 8.0 Hz, 1H,
Ph–H), 6.79 (d, J = 2.0 Hz, 1H, Ph–H), 4.6-5.1 (br, 1H, CH
2
–OH),
4.44 (s, 2H, Ph–CH ).
2
1
Compound 11: H NMR (400 MHz, DMSO): d = 9.64 (s, 1H, Ph–
OH), 7.27 (d, J = 2.0 Hz, 1H, Ph–H), 7.07 (dd, J = 2.0, 8.4 Hz, 1H,
Ph–H), 6.76 (d, J = 8.4 Hz, 1H, Ph–H), 5.10 (t, J = 5.2 Hz, 1H, C–
1
4. General procedure for the reduction of acids to alcohols: Under a N
2
atmosphere, 0.79 g (20 mmol) of NaBH (purity: 96%) and 20 mL of
4
anhydrous tetrahydrofuran were introduced into a 50 mL three-neck
flask equipped with pressure-equalizing addition funnel, a gas inlet
pipe, a thermometer and magnetic stirring bar. The mixture was
2
OH), 4.44 (d, J = 5.2 Hz, 2H, Ph–CH ).
Compound 12: H NMR (400 MHz, DMSO): d = 9.13 (s, 1H, Ph–
OH), 7.13 (d, J = 8.0 Hz, 1H, Ph–H), 6.56–6.59 (m, 2H, Ph–H), 4.84
1
added dropwise with 2.55 g of Me
and stirred for 1 h in an ice-bath and further 4 h at room temperature
until no gas generation was observed. A solution of 10 mmol of acid
2
SO
4
(20 mmol) at 0 °C over 3 min
2 3
(br, 1H, C–OH), 4.43 (s, 2H, Ph–CH ), 2.19 (s, 3H, Ph–CH ).
1
Compound 13: H NMR (400 MHz, DMSO): d = 11.06 (s, 1H, Ph–
OH), 8.15 (d, J = 2.8 Hz, 1H, Ph–H), 7.97 (dd, J = 2.8, 8.8 Hz, 1H,
Ph–H), 6.88 (d, J = 8.8 Hz, 1H, Ph–H), 5.31 (s, 1H, C–OH), 4.45 (s,
and 2.12 g of B(OMe)
added dropwise to the prepared BH
3
in anhydrous tetrahydrofuran (10 mL) was
/THF complex solution at room
3
2
2H, Ph–CH ).
1
temperature over 30 min. The mixture was stirred at the same
temperature for 4.5 h. After the reaction was completed, 10 mL of
Compound 14: H NMR (400 MHz, DMSO): d = 9.81 (s, 1H, Ar-
OH), 7.82 (s, 1H, Ar-H), 7.76 (d, J = 8.0 Hz, 1H, Ar-H), 7.65 (d,
J = 8.0 Hz, 1H, Ar-H), 7.34 (t, J = 7.6 Hz, 1H, Ar-H), 7.24 (t,
J = 7.6 Hz, 1H, Ar-H), 7.11 (s, 1H, Ar-H), 5.17 (s, 1H, C–OH), 4.66
H O was added slowly at 0 °C and the resulting mixture was
2
vigorously stirred for 0.5 h. Then THF was removed on a rotary
evaporator. The residue was extracted with ethyl acetate (3 Â 50 mL),
2
(s, 2H, CH –OH).