Total syntheses of (+)- and (-)-cacospongionolide B: new insight into structural requirements for phospholipase A(2) inhibition.
Total syntheses of (+)- and (-)-cacospongionolide B: new insight into structural requirements for phospholipase A(2) inhibition.
复制标题
DOI：
10.1021/ja026899x
复制
发表时间：
2002-09
影响因子：
15
通讯作者：
Atwood K Cheung;M. Snapper
中科院分区：
文献类型：
--
作者：
Atwood K Cheung;M. Snapper
海绵代谢产物（+）-海绵体皂苷B的首次全合成已在12个线性步骤中完成。关键转化包括三步序列偶联天然产物的两个主要区域以及产生侧链二氢吡喃环。合成类似物对蜂毒磷脂酶A（2）的活性表明，cacospongionaldehyde B与酶具有对映体特异性相互作用，这种相互作用不依赖于γ-羟基丁烯二酸部分。
The first total synthesis of the antiinflammatory marine sponge metabolite (+)-cacospongionolide B has been accomplished in 12 linear steps. The pivotal transformations include a three-step sequence coupling the two main regions of the natural product as well as generating the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A(2) suggests that cacospongionolide B has an enantiospecific interaction with the enzyme that is independent of the gamma-hydroxybutenolide moiety.