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The Configuration of (+)‐8‐Ethylnorlobelol‐I; a Correction of the Literature
Author(s) -
Mill Sibel,
Durant Alex,
Hootelé Claude
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619961220
Subject(s) - chemistry , absolute configuration , piperidine , stereochemistry , stereoselectivity , ketone , nitrone , hydrolysis , alkene , alcohol , carbamate , cycloaddition , organic chemistry , catalysis
The piperidine alkaloid (+)‐8‐ethylnorlobelo‐I is assigned the revised 2 S ,8, S absolute configuration as depicted in 7 . LiAl(O‐ t Bu) 3 H reduction of the ketone rac ‐ 5 proceeded with a high stereoselectivity to give, after hydrolysis of the carbamate function, the syn amino alcohol rac ‐ 6 . Inversion of the C‐8 configuration of ent ‐ 6 yielded (‐)‐8‐ethylnorlobelol‐I ent ‐ 7 . A short nitrone‐alkene‐based synthesis of rac ‐ 7 has been developed.