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Journal articles
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.
https://hal-normandie-univ.archives-ouvertes.fr/hal-02413311
Contributor : Vincent Loisel Connect in order to contact the contributor
Submitted on : Monday, December 16, 2019 - 10:45:13 AM
Last modification on : Thursday, December 2, 2021 - 3:14:59 AM
Contributor : Vincent Loisel Connect in order to contact the contributor
Submitted on : Monday, December 16, 2019 - 10:45:13 AM
Last modification on : Thursday, December 2, 2021 - 3:14:59 AM
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