Chirality and Numbering of Substituted Tropane Alkaloids
Abstract
:1. Introduction
2. Determination of the Configuration Using Optical Properties
3. Determination of the Configuration Using Mosher’s Reagent
1a | 2a ((R)-MTPA ester) | 3a ((S)-MTPA ester) | ||||
---|---|---|---|---|---|---|
d (H) | d (C) | d (H) | d (C) | d (H) | d (C) | |
H–1 | 3.79 (s) | 61.0 | 3.32 (br s) | 60.4 | 3.31 (br s) | 60.8 |
H endo–2 | 2.56-2.45 (m) | 32.1 | 2.14-2.13 (m) | 35.3 | 2.14-2.13 (m) | 35.8 |
H exo–2 | 1.88 (d) (J2exo,2endo = 15) | 1.71-1.67 (m) | 1.72-1.69 (m) | |||
H–3 | 5.05 (s) | 63.0 | 5.05 (t) (J = 4.85) | 65.5 | 5.05 (t) (J = 4.96) | 65.5 |
H endo–4 | 2.56-2.45 (m) | 30.6 | 2.20-2.19 (m) | 34.0 | 2.21-2.20 (m) | 34.4 |
H exo–4 | 2.03 (d) (J4exo,4endo = 15) | 1.93-1.91 (m) | 1.97-1.95 (m) | |||
H–5 | 3.67 (s) | 68.9 | 3.24 (s) | 66.1 | 3.14 (s) | 66.4 |
H–6 | 4.80 (dd) (J6,7exo = 5) | 72.6 | 5.73 (dd) (J6,7endo = 7.48, J6,7exo = 2.97) | 82.0 | 5.76 (dd) (J6,7endo = 7.57, J6,7exo = 2.95) | 82.0 |
H endo–7 | 2.85 (dd) (J7endo,7exo = 10, J7endo,6 = 5) | 37.5 | 2.65 (dd) (J7endo,7exo = 14, J7endo,6 = 7.5) | 35.5 | 2.63 (dd,) (J7endo,7exo = 14, J7endo,6 = 7.9) | 34.8 |
H exo–7 | 2.30-2.25 (m) | 2.12-2.09 (m) | 2.24 (br s) | |||
H3C–N | 2.90 (s) | 37.5 | 2.34 (s) | 40.5 | 2.24 (s) | 40.8 |
H–10 | 5.65 (s) | 115.6 | 5.71 (t) | 116.1 | 5.70 (s) | 116.0 |
(4J = 1.29) | ||||||
H–12 | 2.19 (s) | 20.3 | 2.20 (s) | 20.3 | 2.20 (s) | 20.3 |
H–13 | 1.93 (s) | 27.4 | 1.94 (s) | 27.5 | 1.94 (s) | 27.4 |
H3C–O | 3.56 (s) | 55.4 | 3.58 (s) | 55.4 | ||
H ortho–Ph | 7.55-7.53 (m) | 127.4 | 7.55-7.53 (m) | 127.2 | ||
H meta–Ph | 7.43-7.41 (m) | 128.5 | 7.43-7.41 (m) | 128.4 | ||
H para–Ph | 7.43-7.41 (m) | 129.7 | 7.43-7.41 (m) | 129.6 |
4. Experimental
4.1. Plant Material
4.2. Chemical and Reagents
4.3. Apparatus
4.4. Preparation of Mosher’s Esters
5. Conclusions
Acknowledgements
References
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Humam, M.; Shoul, T.; Jeannerat, D.; Muñoz, O.; Christen, P. Chirality and Numbering of Substituted Tropane Alkaloids. Molecules 2011, 16, 7199-7209. https://doi.org/10.3390/molecules16097199
Humam M, Shoul T, Jeannerat D, Muñoz O, Christen P. Chirality and Numbering of Substituted Tropane Alkaloids. Molecules. 2011; 16(9):7199-7209. https://doi.org/10.3390/molecules16097199
Chicago/Turabian StyleHumam, Munir, Tarik Shoul, Damien Jeannerat, Orlando Muñoz, and Philippe Christen. 2011. "Chirality and Numbering of Substituted Tropane Alkaloids" Molecules 16, no. 9: 7199-7209. https://doi.org/10.3390/molecules16097199