Synthesis of the common propellane core structure of the hasubanan alkaloids |
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Authors: | Nguyen Thong X Kobayashi Yoshihisa |
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Affiliation: | Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive Mail Code 0343, La Jolla, California 92093-0343, USA. |
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Abstract: | The racemic synthesis of the common propellane core structure found in various hasubanan alkaloids is reported. The successful completion hinged upon the stereocontrolled construction of the cis-substituted heterobicycle as a precursor for the intramolecular Dieckmann condensation. A novel strategy is introduced for the facile hydrolysis of a sterically demanding carboxamide under a mild condition. The 2-nitroanilide obtained by the Goldberg arylation of a carboxamide with 2-iodonitrobenzene was readily converted to the corresponding ester derivative by way of N-acylbenzotriazole. We expect that the reported synthetic route will allow the synthesis of a series of hasubanan alkaloids starting from the correspondingly functionalized 2-tetralone derivatives. |
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