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Synthesis of (±)‐Lasubine II Using N ‐Methoxyamines
Author(s) -
Yokoyama Takashi,
Fukami Yutaro,
Sato Takaaki,
Chida Noritaka
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201501143
Subject(s) - piperidine , nitrone , component (thermodynamics) , carbon fibers , chemistry , group (periodic table) , combinatorial chemistry , stereochemistry , organic chemistry , mathematics , physics , cycloaddition , catalysis , algorithm , composite number , thermodynamics
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.