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

Kosaku Tanaka 3rd; Kenichi Kobayashi; Hiroshi Kogen

doi:10.1039/d1cc04290d

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

Chem Commun (Camb). 2021 Sep 23;57(76):9780-9783. doi: 10.1039/d1cc04290d.

Authors

Kosaku Tanaka 3rd¹, Kenichi Kobayashi^{1

2}, Hiroshi Kogen¹

Affiliations

¹ Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan. kkobayashi@hoku-iryo-u.ac.jp.
² Graduate School of Pharmaceutical Sciences, Health Sciences University of Hokkaido, 1757, Kanazawa, Tobetsu, Ishikari, Hokkaido 061-0293, Japan.

PMID: 34486624
DOI: 10.1039/d1cc04290d

Abstract

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.