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Unraveling the biosynthesis of the sporolide cyclohexenone building block.解析sporolide环己烯酮结构单元的生物合成过程。
J Am Chem Soc. 2008 Feb 27;130(8):2406-7. doi: 10.1021/ja710488m. Epub 2008 Jan 31.
3
Synthesis of the sporolide ring framework through a cascade sequence involving an intramolecular [4+2] cycloaddition reaction of an o-quinone.通过涉及邻醌的分子内[4+2]环加成反应的串联序列合成sporolide环骨架。
Angew Chem Int Ed Engl. 2008;47(8):1432-5. doi: 10.1002/anie.200705334.
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Enantioselective total synthesis of (-)-Salinosporamide A (NPI-0052).(-)-盐霉素A(NPI-0052)的对映选择性全合成
Org Lett. 2007 Jun 7;9(12):2289-92. doi: 10.1021/ol0706051. Epub 2007 May 12.
5
Concise total synthesis of (+/-)-salinosporamide A, (+/-)-cinnabaramide A, and derivatives via a bis-cyclization process: implications for a biosynthetic pathway?通过双环化过程对(±)-盐霉素A、(±)-肉桂酰胺A及其衍生物进行简洁的全合成:对生物合成途径有何启示?
Org Lett. 2007 May 24;9(11):2143-6. doi: 10.1021/ol070616u. Epub 2007 May 4.
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Nucleophilic addition to a p-benzyne derived from an enediyne: a new mechanism for halide incorporation into biomolecules.亲核试剂对源自烯二炔的对苯炔的加成反应:卤化物掺入生物分子的新机制。
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Total synthesis of the diazobenzofluorene antibiotic (-)-kinamycin C1.重氮苯并芴抗生素(-)-金霉素C1的全合成。
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Discovery of novel metabolites from marine actinomycetes.从海洋放线菌中发现新型代谢产物。
Curr Opin Microbiol. 2006 Jun;9(3):245-51. doi: 10.1016/j.mib.2006.03.004. Epub 2006 May 3.
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A novel orally active proteasome inhibitor induces apoptosis in multiple myeloma cells with mechanisms distinct from Bortezomib.一种新型口服活性蛋白酶体抑制剂通过不同于硼替佐米的机制诱导多发性骨髓瘤细胞凋亡。
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10
Sporolides A and B: structurally unprecedented halogenated macrolides from the marine actinomycete Salinispora tropica.孢子内酯A和B:来自海洋放线菌热带盐孢菌的结构前所未有的卤代大环内酯类化合物。
Org Lett. 2005 Jun 23;7(13):2731-4. doi: 10.1021/ol050901i.

sporolide B:合成研究。

Sporolide B: Synthetic Studies.

作者信息

Gladding Jeffery A, Bacci James P, Shaw Scott A, Smith Amos B

机构信息

Department of Chemistry, Monell Chemical Senses Center and Laboratory of Research on the Structure of Matter, University of Pennsylvania, Philadelphia, PA 19104, United States.

出版信息

Tetrahedron. 2011 Sep 2;67(35):6697-6706. doi: 10.1016/j.tet.2011.04.094.

DOI:10.1016/j.tet.2011.04.094
PMID:22021939
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3197724/
Abstract

Studies directed towards the synthesis of the architecturally complex marine natural product sporolide B are described. Synthetic analysis suggested advanced hydroquinone and benzodiquinane fragments, which upon elaboration were successfully united via an ester linkage. Macrocyclization studies were then carried out, and although a novel macrocyclization product was obtained, subsequent studies revealed that the tertiary hydroxyls at C(6) and C(10) were sterically encumbered to participate in a successful macrocyclization to furnish sporolide B.

摘要

本文描述了针对结构复杂的海洋天然产物sporolide B的合成研究。合成分析表明了高级对苯二酚和苯并二喹烷片段,经精心构建后通过酯键成功结合在一起。然后进行了大环化研究,虽然得到了一种新型大环化产物,但后续研究表明,C(6)和C(10)位的叔羟基在空间上受到阻碍,无法成功参与大环化反应以生成sporolide B。