In:
European Journal of Organic Chemistry, Wiley, Vol. 2022, No. 36 ( 2022-09-27)
Abstract:
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 (9 S *,11 S *)‐isomer with natural‐type configuration was hyperactive, whereas diastereomeric (9 S *,11 R *)‐isomer was hypoactive upon mice intracerebroventricular injection.
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2022.36
DOI:
10.1002/ejoc.202200669
Language:
English
Publisher:
Wiley
Publication Date:
2022
detail.hit.zdb_id:
1475010-7
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