期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2022, 期 36, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202200669
关键词
Aculeine; Amino acid; Enamide; Neuronal activity; Tryptophan
In this study, we report on the synthetic studies of protoaculeine B, originally proposed structure, isolated from a marine sponge. Starting from tryptophan, two candidates of suitably protected heterotricyclic subunits were synthesized over 8 and 16 steps, respectively. Furthermore, two diastereomeric heterotricyclic amino acids, finally synthesized, were found to have neuroactive properties, with the natural-type configuration being hyperactive and the diastereomeric configuration being hypoactive upon mice intracerebroventricular injection.
Herein, we report our results on the synthetic studies of the originally proposed structure of protoaculeine B, isolated from a marine sponge. Starting from tryptophan, two candidates of the suitably protected heterotricyclic subunits were stereoselectively synthesized over 8 and 16 steps, respectively. Furthermore, two diastereomeric heterotricyclic amino acids, finally synthesized, were found to be neuroactive: the (9S*,11S*)-isomer with natural-type configuration was hyperactive, whereas diastereomeric (9S*,11R*)-isomer was hypoactive upon mice intracerebroventricular injection.
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