Total synthesis of dipiperamide A and revision of stereochemical assignment |
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Authors: | Masaki Takahashi |
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Institution: | School of Pharmacy, Tokyo University of Pharmacy and Life Science, Horinouchi, Hachioji, Tokyo 192-0392, Japan |
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Abstract: | The first total synthesis of dipiperamide A has been achieved by employing a solid-state photodimerization of an (E)-cinnamic acid derivative. This critical step results in the cyclobutane ring, which exists in the natural product, with full control of the regio- and stereochemistry at the four stereogenic centers. Results from these studies indicate that the proposed stereostructure of natural dipiperamide A should be revised to the structure originally assigned to dipiperamide B. |
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Keywords: | Dipiperamide A CYP inhibitor Cyclobutane ring Solid-state photodimerization |
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