Syntheseversuche in der Emetinreihe. 9. Mitteilung. Die absolute Konfiguration von (−)‐2‐Dehydro‐emetin | Zendy

Brossi A. | Zendy; Baumann M. | Zendy; Burkhardt F. | Zendy; Richle R. | Zendy; Frey J. R. | Zendy

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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.

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