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Syntheseversuche in der Emetinreihe. 9. Mitteilung. Die absolute Konfiguration von (−)‐2‐Dehydro‐emetin
Author(s) -
Brossi A.,
Baumann M.,
Burkhardt F.,
Richle R.,
Frey J. R.
Publication year - 1962
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19620450656
Subject(s) - chemistry , absolute configuration , emetine , stereochemistry , optically active , alkaloid , absolute (philosophy) , organic chemistry , medicine , pharmacology , philosophy , epistemology
The synthesis of the four possible optically active 2‐dehydro‐emetines is described and their absolute configuration established. Only one of these isomers, namely (−)‐2‐dehydro‐emetine (IIIa) which has at the two asymmetric centres 11b and 1′ the same absolute configuration as the natural alkaloid (−)‐emetine, shows in vitro and in vivo high amoebicidal activity.