Asymmetric synthesis of 1, 2-dioxolane-3-acetic acids: Synthesis and configurational assignment of plakinic acid a

…, TK Trullinger, X Liu, PH Dussault

文献索引：Dai, Peng; Trullinger, Tony K.; Liu, Xuejun; Dussault, Patrick H. Journal of Organic Chemistry, 2006 , vol. 71, # 6 p. 2283 - 2292

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被引用次数: 45

摘要

The first asymmetric synthesis of 1, 2-dioxolane-3-acetic acids is reported. Key features include the stereoselective opening of enantiomerically enriched oxetanes by hydrogen peroxide, conversion of the resulting 4-hydroperoxy-2-alkanols to 3-alkoxy-1, 2-dioxolanes, and Lewis acid mediated homologation of the latter with a thioester silyl ketene acetal. The approach is modeled on 3, 5-dimethyl-5-hexadecyl-1, 2-dioxolane-3-acetic acid (1a), an ...