Biomimetically inspired total synthesis of (12S)-12-hydroxymonocerin and (12R)-12-hydroxymonocerin |
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| Authors: | Bowen Fang Xingang Xie Peng Jing Changgui Zhao Huilin Li Haichen Ma Xuegong She |
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| Affiliation: | 1. State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 730000, People''s Republic of China;2. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, People''s Republic of China |
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| Abstract: | A concise asymmetric total synthesis of (12S)-12-hydroxymonocerin (1) and (12R)-12-hydroxymonocerin (2) were efficiently achieved from the known 4-bromo-2,6-dimethoxyphenol. The synthetic approach was inspired by our biomimetic synthesis of (+)-monocerin (3) and 7-O-demethylmonocerin (4). The cis-fused furobenzopyranones of 1 and 2 was efficiently constructed via an intramolecular nucleophilic trapping of a quinonemethide intermediate, which was obtained by benzylic oxidation of compound 10 using 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). |
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| Keywords: | Biomimetically inspired total synthesis cis-Fused furobenzopyranone (12S)-12-Hydroxymonocerin (12R)-12-Hydroxymonocerin Anion Relay Chemistry |
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