Asymmetric synthesis of tert-butyl ((1R,4aR,8R,8aR)-1-hydroxyoctahydro-1H-isochromen-8-yl)carbamate |
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| Authors: | Alfonso G Rubia Mateo M Salgado Carlos T Nieto Alejandro Manchado David Díez Francisca Sanz Narciso M Garrido |
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| Institution: | 1. Dpto. de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain;2. X-ray-Diffraction Service from Nucleus, Plaza de los Caídos 1-5, 37008 Salamanca, Spain |
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| Abstract: | The asymmetric synthesis of methyl (E)-4-((1R,2S,3R)-3-amino-2-((E)-2-methoxycarbonyl-eten-1-yl)cyclohexyl)but-2-enoate 14 has been achieved from dimethyl (2E,7E)-nona-2,7-dienedioate 2. A key step is the asymmetric synthesis of 1-hydroxyoctahydro-1H-isochromene derivative 5 whose X-ray analysis corroborated the stereochemistry of the new stereocenters. The asymmetric synthesis of the isochromenyl acetate derivative 11 shows the potential of this methodology for fused cyclohexanic system heterocyclic synthesis. |
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| Keywords: | Corresponding author Tel : +34 666589065 fax: +34 923 294574 |
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