ニトロンの1,3-双極子シクロ付加反応を利用した天然物合成

概要

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Nitrones are well-known to behave as 1, 3-dipoles and readily undergo thermal [3+2] cycloaddition reactions with olefins to produce isoxazolidine derivatives, which can be converted into β-amino alcohols by subsequent reductive N-O bond cleavage. The synthetically significant features of these reactions are carbon-carbon bond formation and introduction of nitrogen and oxygen functionality with concomitant high siteselectivities, regioselectivities, and stereoselectivities. Although this reaction mode has been alloted a more limited role in organic synthesis, more recent studies have demonstrated its general utility in the synthesis of a wide variety of natural products, particularly alkaloids. It is the purpose of this review to indicate the usefulness and synthetic aspects of nitrone methodology applicable to the natural products synthesis.
社団法人有機合成化学協会の論文