（+）-vigulariol 和（-）-sclerophytin A 的全合成。
Total syntheses of (+)-vigulariol and (-)-sclerophytin A.
机构信息
Kenan Laboratory of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, USA.
出版信息
Org Lett. 2011 Sep 16;13(18):4890-3. doi: 10.1021/ol201981j. Epub 2011 Aug 19.
Abstract
The total syntheses of (+)-vigulariol and (-)-sclerophytin A are reported in 15 steps and 16 steps, respectively, from a known compound. The flexible, readily scalable synthetic strategy allows for rapid construction of a critical tricyclic intermediate and is demonstrated via the synthesis of these two marine natural products. A key reaction in this synthetic protocol is a combination Wittig/intramolecular Diels-Alder cycloaddition.
摘要
（+）-vigulariol 和（-）-sclerophytin A 的全合成分别通过 15 步和 16 步反应，从一个已知化合物出发。该灵活、易于扩展的合成策略可快速构建关键的三环中间体，并通过这两种海洋天然产物的合成为例得到了证明。该合成方案中的关键反应是Wittig/分子内 Diels-Alder 环加成反应的组合。
相似文献
1
Total syntheses of (+)-vigulariol and (-)-sclerophytin A.（+）-vigulariol 和（-）-sclerophytin A 的全合成。
Org Lett. 2011 Sep 16;13(18):4890-3. doi: 10.1021/ol201981j. Epub 2011 Aug 19.
2
Total synthesis of the purported structure of sclerophytin F.硬叶藻素F假定结构的全合成。
Org Lett. 2014 Aug 15;16(16):4300-3. doi: 10.1021/ol5020152. Epub 2014 Jul 28.
3
Total synthesis of the supposed structure of (-)-sclerophytin A and an improved route to (-)-7-deacetoxyalcyonin acetate.（-）-硬叶藻素A假定结构的全合成及（-）-7-脱乙酰氧基阿尔辛宁乙酸酯的改进合成路线。
Org Lett. 2000 Aug 24;2(17):2683-6. doi: 10.1021/ol006236p.
4
A general strategy for the synthesis of cladiellin diterpenes: enantioselective total syntheses of 6-acetoxycladiell-7(16),11-dien-3-ol (deacetoxyalcyonin acetate), cladiell-11-ene-3,6,7-triol, sclerophytin A, and the initially purported structure of sclerophytin A.克拉德萜二萜类化合物的合成通用策略：6-乙酰氧基克拉德-7(16),11-二烯-3-醇（去乙酰氧基阿尔西奥宁乙酸酯）、克拉德-11-烯-3,6,7-三醇、硬叶素A以及最初推测的硬叶素A结构的对映选择性全合成。
J Am Chem Soc. 2001 Sep 19;123(37):9033-44. doi: 10.1021/ja016351a.
5
Synthesis of four diastereomers of sclerophytin F and structural reassignment of several sclerophytin natural products.硬叶藻素F的四种非对映异构体的合成及几种硬叶藻素天然产物的结构重新归属
Chemistry. 2015 Mar 16;21(12):4772-80. doi: 10.1002/chem.201406051. Epub 2015 Feb 6.
6
Total asymmetric synthesis of the putative structure of the cytotoxic diterpenoid (-)-sclerophytin a and of the authentic natural sclerophytins A and B.细胞毒性二萜类化合物（-）-硬叶素A以及天然硬叶素A和B的假定结构的全不对称合成。
J Am Chem Soc. 2001 Sep 19;123(37):9021-32. doi: 10.1021/ja011285y.
7
Enantioselective syntheses of authentic sclerophytin A, sclerophytin B, and cladiell-11-ene-3,6,7-triol.天然硬叶蕨素A、硬叶蕨素B和克拉迪-11-烯-3,6,7-三醇的对映选择性合成。
Org Lett. 2001 Jan 11;3(1):135-7. doi: 10.1021/ol000345m.
8
A general strategy for synthesis of both (6Z)- and (6E)-cladiellin diterpenes: total syntheses of (-)-cladiella-6,11-dien-3-ol, (+)-polyanthellin A, (-)-cladiell-11-ene-3,6,7-triol, and (-)-deacetoxyalcyonin acetate.(6Z)-和(6E)-克拉迪菌素二萜类化合物合成的通用策略：(-)-克拉迪拉-6,11-二烯-3-醇、(+)-聚海葵素A、(-)-克拉迪尔-11-烯-3,6,7-三醇和(-)-去乙酰氧基阿尔西奥宁乙酸酯的全合成
J Am Chem Soc. 2006 Dec 13;128(49):15851-5. doi: 10.1021/ja065782w.
9
Approach to the synthesis of cladiell-11-ene-3,6,7-triol.克拉迪尔-11-烯-3,6,7-三醇的合成方法。
Org Lett. 2006 Aug 17;8(17):3663-5. doi: 10.1021/ol061072j.
10
Enantioselective synthesis of (-)-sclerophytin A by a stereoconvergent epoxide hydrolysis.通过立体汇聚环氧化物水解对(-)-石松素 A 进行对映选择性合成。
J Am Chem Soc. 2010 Nov 24;132(46):16380-2. doi: 10.1021/ja108185z. Epub 2010 Oct 28.
引用本文的文献
1
Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.复杂萜类天然产物全合成中的手性源导向合成
Chem Rev. 2017 Sep 27;117(18):11753-11795. doi: 10.1021/acs.chemrev.6b00834. Epub 2017 Mar 15.
2
Bioactive cembranoids from the South China Sea soft coral Sarcophyton elegans.来自中国南海软珊瑚美丽肉芝软珊瑚的生物活性柳珊瑚类化合物。
Molecules. 2015 Jul 22;20(7):13324-35. doi: 10.3390/molecules200713324.
本文引用的文献
1
The natural products chemistry of West Indian gorgonian octocorals.西印度柳珊瑚八放珊瑚的天然产物化学
Tetrahedron. 1995 Apr 17;51(16):4571-4618. doi: 10.1016/0040-4020(95)00216-U. Epub 2001 Feb 1.
2
Asymmetric Aldol-Ring-Closing Metathesis Strategy for the Enantioselective Construction of Six- to Nine-Membered Oxygen Heterocycles.用于对映选择性构建六至九元氧杂环的不对称羟醛-闭环复分解策略。
J Org Chem. 1997 Oct 31;62(22):7548-7549. doi: 10.1021/jo9716688.
3
Enantioselective synthesis of (-)-sclerophytin A by a stereoconvergent epoxide hydrolysis.通过立体汇聚环氧化物水解对(-)-石松素 A 进行对映选择性合成。
J Am Chem Soc. 2010 Nov 24;132(46):16380-2. doi: 10.1021/ja108185z. Epub 2010 Oct 28.
4
Total synthesis of the proposed structure of briarellin J.布瑞来醇 J 的结构的全合成。
Org Lett. 2010 Nov 5;12(21):5028-31. doi: 10.1021/ol102169w.
5
Synthesis and anticancer activity of sclerophytin-inspired hydroisobenzofurans.基于岩白菜素的氢异苯并呋喃的合成及抗癌活性研究。
Bioorg Med Chem Lett. 2009 Dec 15;19(24):6898-901. doi: 10.1016/j.bmcl.2009.10.079. Epub 2009 Oct 22.
6
Strategies for the total synthesis of C2-C11 cyclized cembranoids.C2-C11环化西松烷型二萜类化合物的全合成策略。
Chem Rev. 2008 Dec;108(12):5278-98. doi: 10.1021/cr078117u.
7
Asymmetric total synthesis and X-ray crystal structure of the cytotoxic marine diterpene (+)-vigulariol.细胞毒性海洋二萜（+）-维古拉里醇的不对称全合成及X射线晶体结构
Angew Chem Int Ed Engl. 2008;47(9):1654-7. doi: 10.1002/anie.200704678.
8
An intramolecular Diels-Alder strategy for the asbestinins: enantioselective total syntheses of 11-acetoxy-4-deoxyasbestinin D and asbestinin-12.用于石棉素的分子内狄尔斯-阿尔德策略：11-乙酰氧基-4-脱氧石棉素D和石棉素-12的对映选择性全合成
J Org Chem. 2008 Mar 7;73(5):1649-60. doi: 10.1021/jo0712695. Epub 2007 Oct 5.
9
A concise total synthesis of (+/-)-vigulariol.(±)-维古拉里醇的简洁全合成。
Angew Chem Int Ed Engl. 2007;46(3):437-40. doi: 10.1002/anie.200603880.
10
An intramolecular Diels-Alder approach to the eunicellins: enantioselective total syntheses of ophirin B and astrogorgin.一种用于海扇软珊瑚素的分子内狄尔斯-阿尔德方法：ophirin B和星状柳珊瑚素的对映选择性全合成。
J Am Chem Soc. 2006 Feb 1;128(4):1371-8. doi: 10.1021/ja056334b.
Zotero 插件