3348
A. B. Bueno et al. / Bioorg. Med. Chem. Lett. 17 (2007) 3344–3348
Acknowledgments
16. DIBAH reduction stopped at the aldehyde. Further
reduction with NaBH after removal of the aluminum
salts was necessary to obtain the alcohol.
4
We thank Dr. Maria Luz de la Puente for the HPLC chi-
ral purifications and e.e. determinations. We thank Dr.
Juan F e´ lix Espinosa and Dr. Paloma Vidal for the deter-
mination of the absolute configurations.
1
1
7. Chiral HPLC conditions: Chiracel OJ column, eluting
with 1:1 hexane (0.2% dimethylethylamine)/ethanol at a
1
ml/min flow rate.
8. The enantiomeric excess was analyzed by chiral HPLC
using a Chiralpak AD column, eluting with hexane/
ethanol in isocratic mode (70% of B) at a 1 ml/min flow
rate. Derivative (+)-10 was hydrolyzed to the correspond-
ing acid to determine its ee.
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9
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1
2
results). Cyanide seems to be too big for a and D , but it
1
2
1
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1
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26. Although the affinity of 19 for 5-HT1D is 20-fold
higher than for 5-HT1B or 5-HT1A, we cannot rule out
that this affinity for these receptors (K = 21 and
1
1
i
26 nM, respectively) could be partially responsible for
these differences between 3a and 19 in the serotonin
elevation.
5. Provided by Lancaster.