Synthesis of the stereogenic triad of the halicyclamine A core |
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Authors: | Molander Gary A Cadoret Frédéric |
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Affiliation: | Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, United States |
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Abstract: | We describe herein our progress toward the synthesis of halicyclamine A, which possesses very interesting biological activities and has never been synthesized. For this purpose, we proposed a stereoselective Diels-Alder reaction as a key step for the establishment of the stereogenic triad of the bis(piperidinyl) core of this molecule. A series of NMR studies was then conducted to establish the correct stereochemical assignment subsequent to the Diels-Alder reaction. |
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Keywords: | Total synthesis Marine alkaloid Organotrifluoroborate Stereoselective Diels-Alder reaction Halicyclamine A |
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