Efficient approach to the Azaspirane core of FR 901483 |
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Authors: | Kaden Silvia Reissig Hans-Ulrich |
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Affiliation: | Institut für Chemie und Biochemie, Freie Universit?t Berlin, Takustrasse 3, D-14195 Berlin, Germany. |
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Abstract: | [reaction: see text] An efficient approach to the azaspirane core of FR 901483 is described employing lithiated methoxyallene as a crucial C3 building block and a suitably protected enantiopure ketimine as the second component. The resulting dihydropyrrole derivative was smoothly converted into a spiro keto aldehyde which under acidic conditions provided a novel azanorbornane derivative 15. Under basic reaction conditions, the desired 5-azatricyclo[6.3.1.0(1,5)]dodecane skeleton 16 was generated. The ratio of diastereomers strongly depends on the reaction conditions employed with l-proline in DMSO providing the highest selectivity in favor of one azaspirane product. |
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