Biomimetic Cyclization of Epoxide Precursors of Indole Mono-, Sesqui- and Diterpene Alkaloids by Lewis Acids
スポンサーリンク
概要
- 論文の詳細を見る
Cyclization of the synthesized epoxide precursors of indole mono-, sesqui- and diterpene alkaloids was performed to elucidate the mechanism for biomimetic cationic cyclization to polycyclic structures. 3-(6,7-Epoxygeranyl)indole (11), 3-(10,11-epoxyfarnesyl)indole (2) and 3-(14,15-epoxygeranylgeranyl)indole (3) were respectively synthesized from geraniol, farnesol and geranylgeraniol in 6 or 7 steps. Four Lewis acids (MeAlCl2, BF3·OEt2, TiCl4 and SnCl4) were applied for biomimetic cyclization of the synthesized epoxide precursors. The cyclization products (one product from 11, four products from 2, and three products from 3) were isolated after separation by chromatography. Their structures were determined by using NMR (COSY, HSQC, HMBC, NOESY, etc.) and HRMS analyses. The results show that biomimetic cyclization gave new polycyclic compounds similar to natural indole terpene alkaloids. We conclude that the stability of cation intermediates should determine the preference for product formation by biomimetic cyclization when using a Lewis acid.
論文 | ランダム
- マルチメディア信号処理のVLSI実装による高性能化事例と最新動向 : A 1440×1080 Pixels 30Flames/s Motion-JPEG 2000 Codec for HD-Movie Transmission
- 手術台の変遷(第76回日本医科器械学会大会大会長講演)
- ヒット商品への実践講座 初めて学ぶ電磁振動&騒音設計講座(3)電磁鋼板に発生する磁歪現象の概要
- 歪み波励磁下における電磁鋼板の磁歪推定
- ランセット磁区の計算による電磁鋼板の磁歪の推定