Formal total synthesis of (-)-apicularen a by a strategy based on ring-closing metathesis and transannular cyclization.

Formal total synthesis of (-)-apicularen a by a strategy based on ring-closing metathesis and transannular cyclization.
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通过基于闭环复分解和跨环环化的策略正式全合成 (-)-apularen a。

DOI:
10.1002/asia.200700024
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发表时间:
2007
期刊:
Chemistry, an Asian journal
影响因子:
--
通讯作者:
J. Tae
J. Tae
中科院分区:
--
文献类型:
--
作者:
Young‐Hee Jung;Young;Jieun Lee;J. Tae

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(-)-apicularen A是一种有效的抗肿瘤药物,具有独特的生物学特性,已经完成了15步的合成,从已知的对映体纯羟基过氧化氢开始,使用Jacobsen水解动力学分辨率方法生成。目标物中的12元大环内酯通过合环复合反应生成,羟基烯通过跨环醚化反应生成反式四氢吡喃环体系。
A formal synthesis of (-)-apicularen A, a potent antitumor agent with unique biological properties, has been completed in a 15-step sequence starting from a known, enantiomerically pure hydroxyepoxide, which was generated by using the Jacobsen hydrolytic-kinetic-resolution methodology. The 12-membered macrocyclic lactone in the target was constructed by ring-closing metathesis, and the trans-tetrahydropyran ring system was created through the transannular etherification of a hydroxyalkene.
(-)-apularen A 的正式合成。
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