School of Chemistry and Centre for Biomolecular Sciences, University of St. Andrews, North Haugh, St. Andrews, KY16 9ST, UK.
Org Lett. 2011 Feb 4;13(3):514-7. doi: 10.1021/ol1028699. Epub 2010 Dec 21.
A stereocontrolled total synthesis of (+)-chamuvarinin, isolated from the root extract of Uvaria Chamae, utilizes a convergent modular strategy to construct the adjacently linked C15-C28 ether array, followed by a late-stage Julia-Kocienski olefination to append the butenolide motif. This constitutes the first total synthesis of (+)-chamuvarinin, defining the relative and absolute configuration of this unique annonaceous acetogenin.
从 Uvaria Chamae 的根提取物中分离得到的 (+)-chamuvarinin 的立体控制全合成采用了一种收敛的模块化策略来构建毗邻相连的 C15-C28 醚阵列,然后通过晚期 Julia-Kocienski 烯烃化反应来附加丁烯内酯基序。这是 (+)-chamuvarinin 的首次全合成,确定了这种独特的番荔枝烷酮的相对和绝对构型。