Efficient total synthesis of pulchellalactam,a CD45 protein tyrosine phosphatase inhibitor |
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Authors: | Li Wen-Ren Lin Sung Tsai Hsu Nai-Mu Chern Meei-Shiou |
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Affiliation: | Department of Chemistry, National Central University, Chung-Li, Taiwan 32054, ROC. ch01@ncu.edu.tw |
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Abstract: | A new approach to a CD45 protein tyrosine phosphatase inhibitor, pulchellalactam, is described. The key step of the sequence involves addition and elimination of an enolic lactam in a single step and 70% yield, employing an organocuprate reagent. The resulting alpha,beta-unsaturated lactam could be condensed with isobutyraldehyde to produce Z-pulchellalactam or converted into siloxypyrrole, which was subjected to the BF(3) x Et(2)O-promoted coupling reaction with isobutyraldehyde to afford E-pulchellalactam after E1-cB elimination and TFA deprotection. This first total synthesis afforded Z-pulchellalactam in six steps and 32% overall yield from Boc-glycine. The same sequence of reactions could also be applied to the liquid- or solid-phase synthesis of trifunctionalized pulchellalactam derivatives. |
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