18O 辅助分析 γ,δ-环氧酮环化反应：阿霉素 D 的 C16-C28 片段的合成。
18O assisted analysis of a γ,δ-epoxyketone cyclization: synthesis of the C16-C28 fragment of ammocidin D.
机构信息
Department of Chemistry, Vanderbilt University, Vanderbilt Institute of Chemical Biology, Nashville, Tennessee 37235, USA.
出版信息
Org Lett. 2011 Feb 18;13(4):756-9. doi: 10.1021/ol103003f. Epub 2011 Jan 19.
Abstract
The C16-C28 fragment common to the cytotoxic macrolide ammocidin D has been prepared by a stereospecific 5-exo closure of a γ,δ-epoxyketone followed by a rearrangement to a pyran acetal. The reaction pathway was traced by (18)O labeling of the keto carbonyl and observation of (18)O induced (13)C shifts in the pyran acetal product. NMR data of the synthetic C16-C28 fragment compared favorably to the natural product providing support of the assigned stereochemistry.
摘要
细胞毒性大环内酯氨端霉素 D 的 C16-C28 片段通过γ，δ-环氧酮的立体特异性 5-endo 环化，随后重排为吡喃缩醛而制备。通过酮羰基的（18）O 标记和观察吡喃缩醛产物中（18）O 诱导的（13）C 位移跟踪了反应途径。合成的 C16-C28 片段的 NMR 数据与天然产物非常吻合，为所分配的立体化学结构提供了支持。
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18O assisted analysis of a γ,δ-epoxyketone cyclization: synthesis of the C16-C28 fragment of ammocidin D.18O 辅助分析 γ,δ-环氧酮环化反应：阿霉素 D 的 C16-C28 片段的合成。
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2
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3
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J Antibiot (Tokyo). 2009 Mar;62(3):123-7. doi: 10.1038/ja.2008.23. Epub 2009 Jan 30.
4
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5
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