Synthesis of (±)‐Lasubine II Using N‐Methoxyamines. Issue 4 (30th November 2015)

• Record Type: Journal Article
• Authors: Yokoyama, Takashi; Fukami, Yutaro; Sato, Takaaki; Chida, Noritaka
• Is Part Of: Chemistry, an Asian journal. Volume 11:Issue 4(2016)
• Page Start: 470
• Page End: 473
• Publication Date: 2015-11-30
• Subjects: allylation -- amines -- lasubine -- multicomponent reactions -- total synthesis; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201501143
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: The synthesis of (±)‐lasubine II has been achieved through a three‐component allylation capitalizing on the unique properties of N ‐methoxyamines. This reaction enabled the installation of all the carbon atoms of lasubine II in a single operation. The N ‐methoxy group was efficiently used for the subsequent nitrone formation. A single‐step cyclization of isoxazolidines or N ‐methoxyamines to form functionalized piperidine rings was also developed. Abstract : The synthesis of (±)‐lasubine II has been achieved through a three‐component allylation of an N ‐methoxyamine with an aldehyde and allyltributylstannane in the presence of Lewis acid. The resulting functionalized N ‐methoxyamine was used for nitrone formation or single‐step cyclization to form a piperidine.