Total synthesis of (+/-)-symbioimine |
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Authors: | Zou Yefen Che Qinglin Snider Barry B |
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Institution: | Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA. |
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Abstract: | The synthesis of (+/-)-symbioimine (1) has been completed in only 12 linear steps in 8% overall yield. The key step is the treatment of 13b with BF3.Et2O to generate N-carboalkoxydihydropyridinium cation 14b, which undergoes a novel stereospecific intramolecular Diels-Alder reaction to give adduct 16b in 42% yield. Cleavage of the N-Troc group of 16b afforded imine 24b stereospecifically. Cleavage of the TBDMS ethers and sulfation provided (+/-)-symbioimine (1). reaction: see text]. |
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