Total synthesis of (+/-)-didehydrostemofoline (asparagamine A) and (+/-)-isodidehydrostemofoline |
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Authors: | Brüggemann Markus McDonald Andrew I Overman Larry E Rosen Mark D Schwink Lothar Scott Jeremy P |
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Institution: | Department of Chemistry, 516 Rowland Hall, University of California, Irvine, CA 92697-2025, USA. |
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Abstract: | The first total syntheses of (+/-)-didehydrostemofoline (1) and (+/-)-isodidehydrostemofoline (3) are reported. The synthesis begins with the Diels-Alder reaction of readily available pyrrole 9 and ethyl (E)-3-nitroacrylate, the latter serving as a regioinverted equivalent of ketene. After hydrogenation to prevent retro-Diels-Alder reaction, the major cycloadduct is transformed to 7-azabicyclo2.2.1]heptanol 14. Aza-Cope-Mannich reaction of the formaldiminium derivative of 14 delivers 1-azatricyclo5.3.0.04.10]decane 15, which in 15 additional steps is converted to 1 and 3. |
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