マイクロフロー反応を鍵とする生理活性天然物の実用的合成戦略

概要

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Microfluidic conditions were applied to the acid-mediated reactions, namely, glycosylations, reductive opening of the benzylidene acetal groups, and dehydration, which are the keys to the practical synthesis of N-glycans and immunostimulating natural product, pristane. A distinctly different reactivity from that in the conventional batch stirring was found; the vigorous micromixing of the reactants with the concentrated acids is critical, especially for the “fast” reactions to be successful. Such a common feature might owe to the integration of all favorable aspects of microfluidic conditions, i.e., efficient mixing, precise temperature control, and the easy handling of the reactive intermediate by controlling the residence time. Distinctly different reactivity under microfluidic conditions also led to the success of the large-scale aldol condensation in aqueous biphasic system, as an example of the base-mediated reactions. The microfluidic reactions cited in this review, provoke the need to reinvestigate the traditional or imaginary reactions which have so far been performed and evaluated only in batch apparatus, and therefore, they could be recognized as a new strategy in synthesizing the natural products of the prominent biological activity in a “practical” and an “industrial” manner.
社団法人有機合成化学協会の論文
2010-02-01