A cross-metathesis route to the 5-F(2)-isoprostanes.
A cross-metathesis route to the 5-F(2)-isoprostanes.
复制标题
5-F(2)-异前列烷的交叉复分解途径。
DOI：
10.1021/jo702702s
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发表时间：
2008
期刊：
影响因子：
--
通讯作者：
Snapper,MarcL
中科院分区：
文献类型：
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作者：
Pandya,BhaumikA;Snapper,MarcL
通过官能化双环[3.2.0]庚烯、乙烯和α，β-不饱和酮之间的开环复分解/交叉复分解方案制备八种5-F2-异前列烷的文库。该序列提供了外消旋烯酮的区域和立体选择性的方式，可以通过催化剂控制的不对称还原转化为对映体富集的烯丙醇。侧链的完成，然后通过整体脱保护，导致立体分散途径，以8个对映体富集的5-F2异前列烷。总体而言，从市售4-羟基-2-环戊烯酮经10个步骤合成了该已知和预期的脂质氧化代谢物库。
A library of eight 5-F2-isoprostanes was prepared through a ring-opening metathesis/cross-metathesis protocol between functionalized bicyclo[3.2.0]heptenes, ethylene, and α,β-unsaturated ketones. This sequence provided racemic enones in a regio- and stereoselective fashion that could be converted to enantiomerically enriched allylic alcohols through a catalyst-controlled asymmetric reduction. Completion of the sidechains, followed by global deprotection, resulted in a stereodivergent route to eight enantiomerically enriched 5-F2isoprostanes. Overall, the synthesis of this library of known and anticipated lipid oxidation metabolites was achieved in 10 steps from commercially available 4-hydroxy-2-cyclopentenone.