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Treatment of (±)-sedridine (±)-9a with an excess of Ni/Al alloy in alkaline medium (desulfurization conditions) yielded an 1/1 mixture of C8-epimeric alcohols (±)-sedridine (±)-9a and (±)-allosedridine (±)-23a. For related cases see ref. 3b and Butlin, R. J.; Linney, I. D.; Mahon, M. F.; Tye, H.; Wills, M. J. Chem. Soc., Perkin Trans. 1 1996, 95-105.
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0342527237
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unpublished results
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D+30.9 (MeOH; c 2.0)} by N-acylation and Swern oxidation. Louis, C.; Hootelé, C. unpublished results.
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Louis, C.1
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0003910514
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0343832513
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note
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D+156 (pyridine; c 1.3)}. The discrepancy observed between the values reported for the synthetic and the resolved samples can be ascribed to the low precision of the measurements in this case (±10%).
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4243516107
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X-Ray diffraction analysis of (-)-(Z)-β-styryl p-tolyl sulfoxide 7d revealed that, in the solid state, the sulfur lone pair and the C-C double bond are syn coplanar: Declercq, J. P.; Feneau-Dupont, J.; Louis, C.; Hootelé, C. Acta Cryst. C 1994, 50, 1980-1981.
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48
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0342527234
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in press
-
In this series, optical rotations measured for amino alcohols 23 in ethanol are much lower than those of their epimers 9: Mill, S.; Durant, A.; Hootelé, C. Liebigs Ann. Chem. in press. Therefore we assume that the sign of the specific rotation measured for a mixture of 9 (major) and 23 (minor) refers to 9.
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Liebigs Ann. Chem.
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Mill, S.1
Durant, A.2
Hootelé, C.3
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