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本文引用的文献

1
[5 + 2] cycloaddition reactions in organic and natural product synthesis.有机合成和天然产物合成中的[5 + 2]环加成反应
Chem Rev. 2013 Mar 13;113(3):2244-66. doi: 10.1021/cr300087g. Epub 2012 Nov 15.
2
Natural products from Cephalotaxus sp.: chemical diversity and synthetic aspects.三尖杉属植物的天然产物：化学多样性与合成方面。
Nat Prod Rep. 2012 Aug;29(8):845-69. doi: 10.1039/c2np20037f. Epub 2012 Jun 20.
3
Asymmetric synthesis of the oxygenated polycyclic system of (+)-harringtonolide.(+)-海松醇内酯含氧多环体系的不对称合成。
Org Lett. 2012 Mar 2;14(5):1270-3. doi: 10.1021/ol300133x. Epub 2012 Feb 17.
4
Dual catalysis in enantioselective oxidopyrylium-based [5 + 2] cycloadditions.手性氧化吡喃鎓盐[5+2]环加成反应中的双催化作用。
J Am Chem Soc. 2011 Sep 21;133(37):14578-81. doi: 10.1021/ja206997e. Epub 2011 Aug 25.
5
Synthesis of novel molecular probes inspired by harringtonolide.新型分子探针的合成受海松醇内酯启发。
Org Biomol Chem. 2011 Jun 21;9(12):4570-9. doi: 10.1039/c1ob05299c. Epub 2011 May 3.
6
The nitrosocarbonyl hetero-Diels-Alder reaction as a useful tool for organic syntheses.硝羰杂环[4.3.0]壬-5-烯-2,7-二酮的希夫碱作为有机合成的有用工具。
Angew Chem Int Ed Engl. 2011 Jun 14;50(25):5630-47. doi: 10.1002/anie.201005764. Epub 2011 Apr 21.
7
Further studies of the norditerpene (+)-harringtonolide isolated from Cephalotaxus harringtonia var. drupacea: absolute configuration, cytotoxic and antifungal activities.对从粗榧（Cephalotaxus harringtonia var. drupacea）中分离出的降二萜（+）-三尖杉酯碱的进一步研究：绝对构型、细胞毒性和抗真菌活性。
Planta Med. 2008 Jun;74(8):870-2. doi: 10.1055/s-2008-1074546. Epub 2008 Jun 3.
8
Model studies toward the synthesis of the bioactive diterpenoid, harringtonolide.生物活性二萜类化合物哈林通醇内酯合成的模型研究
Org Biomol Chem. 2007 Aug 21;5(16):2627-35. doi: 10.1039/b707467k.
9
Mild manganese(III) acetate catalyzed allylic oxidation: application to simple and complex alkenes.轻度醋酸锰（III）催化的烯丙基氧化反应：应用于简单烯烃和复杂烯烃
Org Lett. 2006 Jul 6;8(14):3149-51. doi: 10.1021/ol0612298.
10
Catalytic, highly enantio, and diastereoselective nitroso diels-alder reaction.催化、高对映选择性和非对映选择性亚硝基狄尔斯-阿尔德反应。
J Am Chem Soc. 2004 Apr 7;126(13):4128-9. doi: 10.1021/ja049849w.

基于氧化吡喃鎓盐的[5 + 2]环加成反应立体选择性全合成海南洛定醇和哈林通内酯。

Stereoselective total synthesis of hainanolidol and harringtonolide via oxidopyrylium-based [5 + 2] cycloaddition.

机构信息

School of Pharmacy, University of Wisconsin, Madison, Wisconsin 53705, USA.

出版信息

J Am Chem Soc. 2013 Aug 21;135(33):12434-8. doi: 10.1021/ja406255j. Epub 2013 Aug 9.

DOI:10.1021/ja406255j
PMID:23930656
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3798225/
Abstract

The tetracyclic carbon skeleton of hainanolidol and harringtonolide was efficiently constructed by an intramolecular oxidopyrylium-based [5 + 2] cycloaddition. An anionic ring-opening strategy was developed for the cleavage of the ether bridge in 8-oxabicyclo[3.2.1]octenes derived from the [5 + 2] cycloaddition. Conversion of cycloheptadiene to tropone was realized by a sequential [4 + 2] cycloaddition, Kornblum-DeLaMare rearrangement, and double elimination. The biomimetic synthesis of harringtonolide from hainanolidol was also confirmed.

摘要

通过分子内氧化吡喃鎓基 [5 + 2] 环加成反应有效地构建了海南冬酰胺和哈林托内酯的四环碳骨架。开发了一种阴离子开环策略，用于裂解[5 + 2]环加成反应衍生的 8-氧杂双环[3.2.1]辛烷中的醚桥。通过顺序[4 + 2]环加成、Kornblum-DeLaMare 重排和双消除，实现了环庚二烯到吐罗酮的转化。还证实了从海南冬酰胺生物模拟合成哈林托内酯。