使用δ-氨基β-酮膦酸酯和关环复分解反应（RCM）不对称合成碳环核苷砌块（R）-（+）-4-氨基环戊烯酮。
Asymmetric synthesis of the carbocyclic nucleoside building block (R)-(+)-4-aminocyclopentenone using delta-amino beta-ketophosphonates and ring-closing metathesis (RCM).
作者信息
Davis Franklin A, Wu Yongzhong
机构信息
Department of Chemistry, Temple University, Philadelphia, PA 19122, USA.
出版信息
Org Lett. 2004 Apr 15;6(8):1269-72. doi: 10.1021/ol049795v.
PMID:15070314
Abstract
Amino keto-2,7-dienes undergo ring-closing metathesis (RCM) to give 4-aminocyclopentenones, valuable intermediates in the asymmetric construction of carbocyclic nucleosides. The key amino ketodienes were prepared using delta-amino beta-ketophophonates, a new sulfinimine-derived chiral building block, and HWE chemistry. [reaction: see text]
摘要
氨基酮-2,7-二烯进行闭环复分解反应（RCM）生成4-氨基环戊烯酮，这是碳环核苷不对称合成中有价值的中间体。关键的氨基酮二烯是使用δ-氨基β-酮膦酸酯（一种新的亚磺酰亚胺衍生的手性砌块）和HWE化学方法制备的。[反应：见正文]
相似文献
1
Asymmetric synthesis of the carbocyclic nucleoside building block (R)-(+)-4-aminocyclopentenone using delta-amino beta-ketophosphonates and ring-closing metathesis (RCM).
Org Lett. 2004 Apr 15;6(8):1269-72. doi: 10.1021/ol049795v.
2
Convenient route to both enantiomers of a highly functionalized trans-disubstituted cyclopentene. Synthesis of the carbocyclic core of the nucleoside BCA.
J Org Chem. 2005 May 13;70(10):4199-202. doi: 10.1021/jo0502504.
3
A new synthetic route to nucleosides: dissymmetric construction of a cyclopentene system by double [3,3]-sigmatropic rearrangement and double ring-closing metathesis.
Org Lett. 2004 Mar 18;6(6):993-5. doi: 10.1021/ol040006j.
4
Asymmetric synthesis of 2,4,5-trisubstituted piperidines from sulfinimine-derived delta-amino beta-ketoesters. Formal synthesis of pseudodistomin B triacetate.
J Org Chem. 2005 Jul 8;70(14):5413-9. doi: 10.1021/jo050373o.
5
Enantioselective synthesis of cyclic secondary amines through Mo-catalyzed asymmetric ring-closing metathesis (ARCM).
Org Lett. 2003 Dec 11;5(25):4899-902. doi: 10.1021/ol036026n.
6
Synthesis of novel 4'-cyclopropyl-5'-norcarbocyclic adenosine phosphonic acid analogues.
Nucleosides Nucleotides Nucleic Acids. 2010 Nov;29(11):905-19. doi: 10.1080/15257770.2010.535802.
7
Asymmetric synthesis of new beta,beta-difluorinated cyclic quaternary alpha-amino acid derivatives.
Org Lett. 2006 Aug 31;8(18):4129-32. doi: 10.1021/ol061733c.
8
An Evans-Tishchenko-ring-closing metathesis approach to medium-ring lactones.
Org Lett. 2007 Feb 15;9(4):631-4. doi: 10.1021/ol062932z. Epub 2007 Jan 27.
9
Practical synthesis of D-cyclopent-2-enone, the key intermediate of carbocyclic nucleosides.
Nucleosides Nucleotides Nucleic Acids. 2003 May-Aug;22(5-8):771-3. doi: 10.1081/NCN-120022631.
10
Total synthesis of (+)-phomopsolide C by ring-size selective ring-closing metathesis/cross-metathesis.
Org Lett. 2005 Nov 24;7(24):5513-6. doi: 10.1021/ol052332k.
引用本文的文献
1
Recent trends in the direct oxyphosphorylation of C-C multiple bonds.
RSC Adv. 2020 Dec 23;11(1):470-483. doi: 10.1039/d0ra08074h. eCollection 2020 Dec 21.
2
Efficient synthesis of β'-amino-α,β-unsaturated ketones.
Beilstein J Org Chem. 2013;9:486-95. doi: 10.3762/bjoc.9.52. Epub 2013 Mar 6.
3
A greener enantioselective synthesis of the antiviral agent North-methanocarbathymidine (N-MCT) from 2-deoxy-d-ribose.
Tetrahedron. 2009 Oct 10;65(41):8461-8467. doi: 10.1016/j.tet.2009.08.035.
4
Synthesis of polysubstituted pyrroles from sulfinimines (N-sulfinyl imines).
Tetrahedron. 2008 May 5;64(19):4174-4182. doi: 10.1016/j.tet.2008.02.102.
5
Asymmetric synthesis of polyfunctionalized pyrrolidines from sulfinimine-derived pyrrolidine 2-phosphonates. Synthesis of pyrrolidine 225C.
Org Lett. 2006 May 25;8(11):2273-6. doi: 10.1021/ol060521c.
Zotero 插件