- 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-exoor 6-endocyclization. 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.
- Tanaka, Kosaku,Kobayashi, Kenichi,Kogen, Hiroshi
-
p. 9780 - 9783
(2021/09/30)
-
- Short synthesis of berkeleyamide D and determination of the absolute configuration by the vibrational circular dichroism exciton chirality method
-
The first synthesis of (±)-berkeleyamide D has been accomplished. The key features of this synthesis include the formation of an α,β-epoxy-γ-lactam via a Darzens reaction and the construction of a spirocyclic ring system by a C-acylation reaction followed by an intramolecular spirocyclization via an epoxide-opening reaction. Following optical resolution by chiral HPLC, the absolute configurations of both enantiomers of berkeleyamide D were determined by the vibrational circular dichroism exciton chirality method.
- Komori, Kenta,Taniguchi, Tohru,Mizutani, Shoma,Monde, Kenji,Kuramochi, Kouji,Tsubaki, Kazunori
-
supporting information
p. 1386 - 1389
(2014/04/03)
-