使用手性蒽辅助剂对坎德那宁B和C进行对映选择性合成。
Enantioselective syntheses of candenatenins B and C using a chiral anthracene auxiliary.
作者信息
Jones Amanda L, Liu Xiang, Snyder John K
机构信息
Center for Chemical Methodology and Library Development and the Department of Chemistry, Boston University, 590 Commonwealth Ave., Boston, Massachusetts, 02215.
出版信息
Tetrahedron Lett. 2010 Feb 17;51(7):1091-1094. doi: 10.1016/j.tetlet.2009.12.108.
Abstract
An asymmetric synthesis of two anticancer natural products, candenatenins B and C, is described, leading to a revision of the originally assigned stereochemistry. The synthesis follows a Diels-Alder/retro-Diels Alder strategy using a chiral anthracene auxiliary to access both targets with 90% ee. The inherent structural qualities of the auxiliary allow for both regio- and diastereoselective transformations.
摘要
描述了两种抗癌天然产物坎德奈宁B和C的不对称合成，从而对最初指定的立体化学进行了修正。该合成采用狄尔斯-阿尔德/逆狄尔斯-阿尔德策略，使用手性蒽辅助剂以90%的对映体过量获得两个目标产物。辅助剂的固有结构特性允许区域和非对映选择性转化。
相似文献
1
Enantioselective syntheses of candenatenins B and C using a chiral anthracene auxiliary.
Tetrahedron Lett. 2010 Feb 17;51(7):1091-1094. doi: 10.1016/j.tetlet.2009.12.108.
2
Enantioselective Synthesis of Axially Chiral Biaryls by Diels-Alder/Retro-Diels-Alder Reaction of 2-Pyrones with Alkynes.
J Am Chem Soc. 2021 Jun 23;143(24):8993-9001. doi: 10.1021/jacs.1c04759. Epub 2021 Jun 9.
3
A new chiral anthracene for the asymmetric Diels-Alder/retro-Diels-Alder sequence.
Org Lett. 2005 Jan 6;7(1):31-4. doi: 10.1021/ol047968a.
4
(1R)-(+)-camphor and acetone derived alpha'-hydroxy enones in asymmetric Diels-Alder reaction: catalytic activation by Lewis and Brønsted acids, substrate scope, applications in syntheses, and mechanistic studies.
J Org Chem. 2010 Mar 5;75(5):1458-73. doi: 10.1021/jo9023039.
5
Enantioselective synthesis of allylic alcohols via an oxazaborolidinium ion catalyzed Diels-Alder/Retro-Diels-Alder sequence.
Org Lett. 2009 Nov 19;11(22):5358-61. doi: 10.1021/ol902280d.
6
Chiral hetero Diels-Alder products by enantioselective and diastereoselective zirconium catalysis. Scope, limitation, mechanism, and application to the concise synthesis of (+)-Prelactone C and (+)-9-deoxygoniopypyrone.
J Am Chem Soc. 2003 Apr 2;125(13):3793-8. doi: 10.1021/ja028186k.
7
Enantioselective Synthesis of Arene cis-Dihydrodiols from 2-Pyrones.
Angew Chem Int Ed Engl. 2019 Oct 7;58(41):14562-14567. doi: 10.1002/anie.201908284. Epub 2019 Aug 29.
8
Diene-Transmissive Enantioselective Diels-Alder Reactions and Sequences Involving Substituted Dendralenes.
J Org Chem. 2019 Nov 15;84(22):14712-14723. doi: 10.1021/acs.joc.9b02296. Epub 2019 Oct 29.
9
Highly Enantioselective Synthesis Using Prolinol as a Chiral Auxiliary: Silver-Mediated Synthesis of Axially Chiral Vinylallenes and Subsequent (Hetero)-Diels-Alder Reactions.
Org Lett. 2019 Oct 4;21(19):7717-7721. doi: 10.1021/acs.orglett.9b02514. Epub 2019 Sep 25.
10
Application of the aza-Diels-Alder reaction in the synthesis of natural products.
Org Biomol Chem. 2017 Apr 11;15(15):3105-3129. doi: 10.1039/c6ob02761j.
本文引用的文献
1
Enantioselective synthesis of allylic alcohols via an oxazaborolidinium ion catalyzed Diels-Alder/Retro-Diels-Alder sequence.
Org Lett. 2009 Nov 19;11(22):5358-61. doi: 10.1021/ol902280d.
2
Candenatenins A-F, phenolic compounds from the heartwood of Dalbergia candenatensis.
J Nat Prod. 2009 Aug;72(8):1395-8. doi: 10.1021/np900077h.
3
Understanding the stereoselection induced by chiral anthracene templates in Diels-Alder cycloaddition: a DFT study.
J Org Chem. 2009 Mar 20;74(6):2328-36. doi: 10.1021/jo802365v.
4
Anthracene cycloadducts as highly selective chiral auxiliaries.
J Org Chem. 2008 Apr 4;73(7):2935-8. doi: 10.1021/jo702724t. Epub 2008 Mar 6.
5
Highly diastereoselective Diels-Alder cycloadditions of 9R-(1-methoxyethyl)anthracene with p-benzoquinone.
Org Biomol Chem. 2006 Jun 7;4(11):2296-303. doi: 10.1039/b603819k. Epub 2006 May 8.
6
Anti-inflammatory neolignans from Piper kadsura.
J Nat Prod. 2006 May;69(5):842-4. doi: 10.1021/np0505521.
7
Heterocyclic ring scaffolds as small-molecule cholesterol absorption inhibitors.
Org Biomol Chem. 2005 Oct 7;3(19):3514-23. doi: 10.1039/b510100j. Epub 2005 Aug 24.
8
Chiral anthracene and anthrone templates as stereocontrolling elements in Diels-Alder/retro Diels-Alder sequences.
Bioorg Med Chem. 2005 Sep 1;13(17):5299-309. doi: 10.1016/j.bmc.2005.06.025.
9
A new chiral anthracene for the asymmetric Diels-Alder/retro-Diels-Alder sequence.
Org Lett. 2005 Jan 6;7(1):31-4. doi: 10.1021/ol047968a.
10
High-pressure selectivity studies--a simple route to a homochiral wistarin precursor.
Chemistry. 2003 Aug 18;9(16):3849-58. doi: 10.1002/chem.200204524.
Zotero 插件