摘要
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 α,β-unsaturated lactam could be condensed with isobutyraldehyde to produce Z-pulchellalactam or converted into siloxypyrrole, which was subjected to the BF3·Et2O-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.
原文 | ???core.languages.en_GB??? |
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頁(從 - 到) | 4702-4706 |
頁數 | 5 |
期刊 | Journal of Organic Chemistry |
卷 | 67 |
發行號 | 14 |
DOIs | |
出版狀態 | 已出版 - 12 7月 2002 |