Xu Tianxiang, Leng Xiao, S. Huang
2016
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Abstract
One concise methods for synthesis of oxetan-3-ol from epoxy chloropropane are reported. The method involve employsepoxy chloropropane opening of reaction, esterifiction, electrophilic reaction, ring-closure reaction. Fig. 1 Structure of oxetan-3-ol and the related molecule. Oxetan-3-ol is usually used for the preparation of 3-oxetanone. and the compounds containing such oxetanone moiety have been often used in synthetic and medicinal chemistry. Recently, Carreira and coworkers explored to use the oxetanone unit as a gem-dimethyl variant to modify solubility, lipophilicity, metabolic stability, and molecular conformation (3). . Oxetan-3-ones are also useful in synthesis and drug discovery and can serve as precursors to oxetanones, as well as oxetan-3-one, 1,3-epoxy-2-propanone, and other oxetane derivatives are also useful in serving as precursors to oxetanones (4). Chemerda et. al also reported that steroids involving oxetan-3-ones possessed novel bioactivity, such as antiinflammatory and antiglucocorticoid (5). Owing to the considerable diversity of possible oxetanthe synthetic approaches to oxetan-3-ol was urgent to develop, and actually there are a limited number of routes described. Recently, Zhang reported gold catalyzed oxidative cyclization of propargyl alcohol (6). Ryono et. al developed a four steps route to construct oxetan-3-ol (7). We believed an efficient and concise route to synthesize this useful oxetane is necessary. So based on A's report, we developed a modified approach to obtain oxetan-3-ol. Our retrosynthesis was depicted in Figure 2. The target oxetan-3-ol was disconnected to protected (2). The intermediate (2) was devised to obtain from chloride (3) via two steps via a hydrolysis and an intramolecular cyclization. For synthesis of (3), it would be disconnected to alcohol (4) through a protection. The later was designed to be got from commercially available epoxy chloropropane (5).