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Concise synthesis of (+)-serinolamide A
Authors:Ya-Ru Gao  Shi-Huan GuoZhuan-Xiang Zhang  Shuai MaoYan-Lei Zhang  Yong-Qiang Wang
Affiliation:Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710069, PR China; Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, Shanghai 200032, PR China
Abstract:Serinolamide A, isolated from a species of marine cyanobacteria, exhibits a moderate agonist effect and selectivity for the CB1 cannabinoid receptor, which is unusual for marine natural products. Herein, we reported a highly efficient enantiospecific first total synthesis of (+)-serinolamide A from l-serine in nine steps with 30% overall yield. The synthesis method provides a facile, practicable, and economical approach for the preparation of other similar endocanabinoid lipids.
Keywords:Total synthesis   Serinolamide A   l-Serine   Fatty acid   Endocanabinoid lipids
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