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

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. D...

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Bibliographic Details
Published in:Tetrahedron 2016-06, Vol.72 (23), p.3221-3231
Main Authors: Šafář, Peter, Marchalín, Štefan, Prónayová, Nadežda, Vrábel, Viktor, Lawson, Ata Martin, Othman, Mohamed, Daïch, Adam
Format: Article
Language:English
Subjects:
6-Oxopipecolinic acid
Alkaloids
Biocompatibility
Chemical Sciences
Diastereoselective reduction
Nitrogen atoms
Phenanthroquinolizidine alkaloids
Pools
Reduction
Residues
Synthesis
Tetrahedrons
Thienoquinolizidine
π-Cationic cyclization
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
0040-4020
DOI:10.1016/j.tet.2016.04.047