Stereocontrolled total synthesis of (+)-pederine |
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| Affiliation: | 1. Acute Critical Illness Center,Jinshan Hospital, Fudan University, 1508 Longhang Road, Shanghai 201508, China;2. Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, China;3. Department of Pharmacy, Shanghai First Maternity and Infant Hospital, Tongji University School of medicine, Shanghai 201204, China |
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| Abstract: | A mild one-pot method for the synthesis of acyclic N-(1-methoxyalkyl)amides starting from carboxylic acid and methyl imidates has been developed and applied to the first total synthesis of (+)-pederine (1), a potent insect poison. Furthermore, the stereocontrolled total synthesis of 1 was also achieved by employing acid catalyzed double alkoxy-exchange reaction of N-(1 -methoxylakyl)amide group as key step. |
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