期刊
RSC ADVANCES
卷 12, 期 19, 页码 11613-11618出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ra01537d
关键词
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资金
- NIH [P01-GM095467]
The first total convergent synthesis of a key fatty acid is described, confirming the native epoxydocosahexaenoic acid as the biosynthetic precursor of important signaling molecules in the resolution of inflammation.
The first total convergent synthesis of 4(S),5(S)-oxido-17(S)-hydroxy-6(E),8(E),10(Z),13(Z),15(E),19(Z)-docosahexaenoic acid (1) is described. The reported synthesis led to confirmation of the native epoxydocosahexaenoic acid as the biosynthetic precursor of lipid mediators resolvin D3 and resolvin D4. These potent enzymatic products of docosahexaenoic acid (DHA) are important signaling molecules in the resolution of inflammation. A stereocontrolled and chiral pool-based synthetic strategy was employed, with key features including epoxide transposition under basic conditions to form the oxirane ring, and a cis-selective Wittig reaction to secure the target docosahexaenoate backbone.
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