期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 82, 期 4, 页码 2032-2039出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02870
关键词
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资金
- JSPS KAKENHI [JP15H05904]
- Kobayashi International Scholarship
Resolvin D5 (RvDS) is a metabolite of docosahexanoic acid with anti-inflammatory activity that has not yet been thoroughly investigated because of its low biological availability. A synthetic route to optically active RvD5 was developed by assembling the C1-C10 aldehyde, C11-C13 phosphonium salt, and C14-C22 aldehyde building blocks. The aldehyde fragments were prepared by Sharpless asymmetric epoxidation of corresponding racemic (E)-1-TMS-1-alken-3-ols followed by reaction of the TBS ethers of the resulting epoxy alcohols with Et(2)A1CN and DIBAL reduction of the (E)-1-cyano-1-alken-3-ol derivatives. The C14-C22 aldehyde was connected with the C11-C13 fragment, i.e., [TBSO(CH2)(3)PPh3](+) Br-, by Wittig reaction. The resulting C11-C22 intermediate was converted to the phosphonium salt, which was attached to the C1-C10 aldehyde by Wittig reaction to yield the structure of RvD5.
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