Enantioselective total synthesis of (+)-rubrobramide, (+)-talaramide A, and (−)-berkeleyamide D by a skeletal diversification strategy

A unified synthesis of (+)-rubrobramide, (+)-talaramide A, and (−)-berkeleyamide D was achieved from the vinylogous esters by a skeletal diversification strategy based on regioselective 5- exo or 6- endo cyclization. This report describes the first enantioselective total synthesis of (+)-rubrobramid...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2021-09, Vol.57 (76), p.978-9783
Main Authors: Tanaka, Kosaku, Kobayashi, Kenichi, Kogen, Hiroshi
Format: Article
Language:English
Subjects:
Alzheimer's disease
Amides
Enantiomers
Esters
Synthesis
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Summary:A unified synthesis of (+)-rubrobramide, (+)-talaramide A, and (−)-berkeleyamide D was achieved from the vinylogous esters by a skeletal diversification strategy based on regioselective 5- exo or 6- endo cyclization. This report describes the first enantioselective total synthesis of (+)-rubrobramide and (+)-talaramide A. Additionally, synthetic spirocyclic lactam compounds, including (−)-berkeleyamide D, showed moderate inhibitory activity against amyloid-β aggregation for the potential treatment of Alzheimer's disease. A unified synthesis of (+)-rubrobramide, (+)-talaramide A, and (−)-berkeleyamide D was achieved from the vinylogous esters by a skeletal diversification strategy based on regioselective 5- exo or 6- endo cyclization.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc04290d