Stereoselective synthesis of the cis-275B decahydroquinoline ring system |
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| Authors: | Edith J Banner |
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| Institution: | Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA |
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| Abstract: | The Diels-Alder precursor was constructed from readily available d-glutamic acid utilizing a series of functional group transformations. The stereocenter of the amino acid provided the desired stereochemistry at C2 and diastereoselectively directed the intramolecular Diels-Alder cyclization. This simultaneously generated the three remaining stereocenters and yielded a bicyclic intermediate with all four stereocenters of the target decahydroquinoline 275B. |
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| Keywords: | Alkaloids Decahydroquinolines Diels-Alder reaction |
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