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Use of chiral-pool approach into epi-thieno analogues of the scarce bioactive phenanthroquinolizidine alkaloids

Abstract : The stereoselective synthesis of epi-thieno analogues of the phenanthroquinolizidine bioactive alkaloids (-)-Cryptopleurine and (-)-(15R)-Hydroxycryptopleurine was achieved in five steps starting from easily available enantiopure (S)-2-aminoadipic acid used as chiral pool and nitrogen atom source. During these investigations, both π-cationic cyclization of chiral N-thienylmethyl-6-oxopipecolinic acids into pure (S)-keto-lactams and theirs regioselective and diastereoselective reduction, considered as key steps of this sequence, were studied. Of particular interest, the Friedel-Crafts cyclization using (CF3CO)2O/BF3·Et2O show that near the expected keto-lactams, enamides and enamidones containing trifluoromethyl residue were isolated. A mechanism leading to the latter products with high synthetic potential was discussed. © 2016 Published by Elsevier Ltd.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02413311
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Submitted on : Monday, December 16, 2019 - 10:45:13 AM
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Peter Šafář, Štefan Marchalín, Nadežda Prónayová, Viktor Vrábel, Ata Martin Lawson, et al.. Use of chiral-pool approach into epi-thieno analogues of the scarce bioactive phenanthroquinolizidine alkaloids. Tetrahedron, Elsevier, 2016, 72 (23), pp.3221-3231. ⟨10.1016/j.tet.2016.04.047⟩. ⟨hal-02413311⟩

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