Efficient total synthesis of pulchellalactam, a CD45 protein tyrosine phosphatase inhibitor

Wen Ren Li, Sung Tsai Lin, Nai Mu Hsu, Meei Shiou Chern

研究成果: 雜誌貢獻期刊論文同行評審

88 引文 斯高帕斯(Scopus)

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???
頁(從 - 到)4702-4706
頁數5
期刊Journal of Organic Chemistry
67
發行號14
DOIs
出版狀態已出版 - 12 7月 2002

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