Synthetic Efforts Towards the Synthesis of the Complex Diterpene Providencin
Synthetic Efforts Towards the Synthesis of the Complex Diterpene Providencin
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DOI：
10.1055/s-0028-1216728
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发表时间：
2009-06-03
期刊：
影响因子：
2
通讯作者：
Mulzer, Johann
中科院分区：
文献类型：
--
作者：
Gaich, Tanja;Weinstabl, Harald;Mulzer, Johann
普罗维菌素是一种新型的高含氧海洋呋喃膜内酯，具有环丁烷环和高度应变的7，8-反式环氧化物。报道了各种全合成或该化合物的合成方法。环丁烷部分通过[2+2]环加成反应生成，呋喃环通过Wipf钯催化的烷酮环化反应生成。大环环通过Horner-Wadsworth-Emmons烯化或闭环复分解闭合。然而，后一种反应只生成不需要的7，8-Z-烯烃，到目前为止，转化为E-异构体的反应还没有成功。
Providencin is a novel, highly oxygenated marine furanocembranolide featuring a cyclobutane ring and a highly strained 7,8-trans-epoxide. Various approaches to the total synthesis or this compound are reported. The cyclobutane moiety is generated via [2+2] cycloaddition and the furan ring is constructed via a Wipf palladium-catalyzed alkynone cyclization. The macrocyclic ring is closed via a Horner-Wadsworth-Emmons olefination or ring-closing metathesis. The latter reaction, however, produces the undesired 7,8-Z-oleFin exclusively, and the conversion into the E-isomer has been, thus far, unsuccessful.