6 1,2-不斉誘起反応による1,2-ジオール誘導体の立体選択的合成 : 光学活性なexo-ならびにendo-ブレビコミンの合成

概要

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Four possible stereoisomers of vicinal diol derivatives were synthesized stereoselectively by nucleophililc addition to optically activeα-alkoxy-β-trimethylsilyl-β,γ-unsaturated carbonyl compounds. Thus, (R)- and (S)-2-alkoxy-3-trimethylsilylalk-3-enals 4 react with Grignard reagents to afford syn-5 with >93% selectivity, and syn-4 thus prepared can be readily converted to >99% pure anti-5 via oxidation and subsequent reduction of the resulting ketones 6 with L-Selectride (Scheme 1). Both (R)- and (S)-2-alkoxy-3-trimethylsilylalk-3-enals 4 were selectively synthesized starting with (R)-O-isopropylidene glyceraldehyde 7. The utility of the present reaction is also demonstrated by the preparation of exo- and endo-brevicomin.
天然有機化合物討論会の論文
1985-09-07