Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Reviews and Accounts
A New Paradigm for Practical Synthesis of Biofunctional Natural Products: Renaissance of Traditional Organic Reactions under Microfluidic Conditions
Katsunori Tanaka
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2010 Volume 68 Issue 2 Pages 124-135

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Abstract

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.

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© 2010 The Society of Synthetic Organic Chemistry, Japan
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