ChemInform Abstract: Synthesis of Enantiomerically Enriched 2,5-Dihydrofuran Derivatives from Easily Available Enantiomerically Enriched 2-Butyne-1,4-diols by Stereospecific Transformation.
✍ Scribed by Hiroyuki Saimoto; Masaru Yasui; Shin-ichiro Ohrai; Hiroshige Oikawa; Kazuhiro Yokoyama; Yoshihiro Shigemasa
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 34 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Synthesis of Enantiomerically Enriched 2,5-Dihydrofuran Derivatives from Easily Available Enantiomerically Enriched 2-Butyne-1,4-diols by Stereospecific Transformation.
-The enantiomerically enriched butynols (IV) and (X) are prepared by enantioselective reduction of keto alcohols (I) and (VII) without protection of the hydroxy group, followed by acylation or pivaloylation. The transformation of (IV) and (X) into the dihydrofurans (V) and (XI) is achieved with complete stereospecificity by an Ag(I)-mediated rearrangement of the monoesters (IV) and (X) to allenic intermediates, followed by Ag(I)-assisted cyclization. A formal synthesis of (S)-(-)-ascofuranone is achieved using this sequence.