Asymmetric syntheses of (−)-isoretronecanol and (−)-trachelantamidine |
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Authors: | Marta Brambilla Stephen G DaviesAi M Fletcher Paul M RobertsJames E Thomson |
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Institution: | Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK |
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Abstract: | Short and concise total asymmetric syntheses of (−)-isoretronecanol and (−)-trachelantamidine are reported. Oxidative cleavage of tert-butyl (S,S,S,Z)-7-N-benzyl-N-(α-methylbenzyl)amino]cyclohept-3-ene-1-carboxylate, followed by hydrogenolysis promoted in situ cyclisation/reduction, which provided rapid access to the bicyclic core within (−)-isoretronecanol. Analogous treatment of the C(1)-epimer gave (−)-trachelantamidine. Overall, the syntheses of (−)-isoretronecanol and (−)-trachelantamidine were completed in eight and seven steps and 20 and 9.5% yield, respectively, from commercially available starting materials. |
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Keywords: | (&minus )-Isoretronecanol (&minus )-Trachelantamidine Lithium amide Conjugate addition Asymmetric synthesis Pyrrolizidine alkaloids |
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