State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui South Road, Lanzhou, Gansu 730000, China.
J Org Chem. 2011 May 20;76(10):4075-81. doi: 10.1021/jo102511x. Epub 2011 Apr 1.
Through a biomimetic pathway, hyperolactone D, 4-hydroxyhyperolactone D, and hyperolactone C were synthesized from methyl acetoacetate via Weiler's dianion method, asymmetric allylic alkylation, biomimetic lactonization, oxidation, and cyclization. The stereochemistry of the quaternary carbon was controlled efficiently by Palladium-catalyzed asymmetric allylic alkylation. This strategy was also used for the synthesis of hyperolactone B.
通过仿生途径，从甲基乙酰乙酸酯出发，经 Weiler 二负离子法、不对称烯丙基烷基化、仿生内酯化、氧化和环化反应，合成了 hyperolactone D、4-hydroxyhyperolactone D 和 hyperolactone C。通过钯催化的不对称烯丙基烷基化反应有效地控制了季碳原子的立体化学。该策略也用于 hyperolactone B 的合成。
