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有機セレン試薬の新展開とその天然物合成への応用

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概要 Modern organoselenium chemistry was born in 1973, since then a variety of organoselenium reagents, e.g., diphenyl diselenide, phehyl selenide anion, benzeneselenenyl halides, sodium benzeneselenolate,... etc., have been developed and widely used in organic synthesis. The explosive growth of organoselenium chemistry during the past two decades is undoubtedly attributed to the specific properties of organic selenium molecules. Among these organoselenium reagents, "phenyl selenide anion", which is readily prepared by the reduction of diphenyl diselenide with sodium borohydride in ethanol according to the Sharpless' protocol, has been extensively used in organic synthesis as the most common and useful selenium reagent. However most of these organoselenium reagents have been mainly used so far as means to introduce double bonds wherein selenofunction is once incorporated into substrates and in turn selenocompounds formed are converted to olefins by oxidation or elimination reactions. This lecture will introduce new developments of organoselenium reagents in organic synthesis, particularly new type of reactions in which selenofunction is not incorporated into substrates. We focused on the electron donating character of extremely soft selenium atom and designed its use as reducing agents. Thus the organoselenium reagents such as "phenyl selenide anion" and benzeneselenol were discovered to act as excellent reducing agents for conversion of various α, β-epoxy ketones, α, β-epoxy esters, epoxy lactones, and lactams tothe corresponding β-hydroxy carbonyl compounds (aldols). The organoselenium-mediated reduction newly developed provides a promising entry to a wide variety of cyclic and acyclic aldols and their analogs. We also discuss the exact structure of "phenyl selenide anion" whish has been used as the most common and representative selenium reagent in organic synthesis since its discovery in 1973. The lecture also presents applications of the organoselenium-mediated reduction to natural product synthesis including Santanolides, Diarylheptanolides, Picrotoxinin and Picrotin.続きを見る

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登録日 2009.04.22
更新日 2017.05.10

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