Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2022, Issue 36, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202200669
Keywords
Aculeine; Amino acid; Enamide; Neuronal activity; Tryptophan
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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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