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Total synthesis of (+)-trans- dihydronarciclasine from (+)-7-azabicyclo[2.2.1]heptanone |
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| Authors: | Ganesh Pandey Rushil Fernandes Debasis Dey Binoy Majumder |
| Institution: | 1. Molecular Synthesis Laboratory, Center of Biomedical Research, Sanjay Gandhi Post Graduate Institute of Medical Sciences Campus, Raebareli Road, Lucknow, 226014, U. P., India;2. Division of Organic Chemistry, National Chemical Laboratory, Pune, 411008, India |
| Abstract: | A concise asymmetric total synthesis of Amaryllidaceae alkaloid (+)-trans-dihydronarciclasine is accomplished starting from optically pure 7-azabicyclo2.2.1]heptanone scaffold in 13 linear steps. Key features of the strategy include substrate-directed stereoselective installation of the trans B-C ring junction and regioselective Wacker-type internal olefin oxidation to provide a rapid access to all hydroxyl functionalities over the key cyclohexane ring in a stereocontrolled manner. |
| Keywords: | Amaryllidaceae alkaloids 7-Deoxy-pancrastatin Wacker-type internal olefin oxidation |
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