抗肿瘤大环内酯类化合物劳利霉素C-C片段的对映选择性合成。
An enantioselective synthesis of the C-C segment of antitumor macrolide laulimalide.
作者信息
Ghosh Arun K, Wang Yong
机构信息
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607, USA.
出版信息
Tetrahedron Lett. 2000 Apr 1;41(14):2319-2322. doi: 10.1016/S0040-4039(00)00158-1. Epub 2002 Aug 2.
Abstract
An enantioselective synthesis of the C-C segment of the novel antitumor agent laulimalide is described. The key steps involve a highly diastereoselective allylation, ring-closing olefin metathesis of a homoallylic alcohol derived acrylate ester, a stereoselective anomeric alkylation and an elaboration of an -methylene unit by a Julia olefination reaction.
摘要
描述了新型抗肿瘤药物劳利霉素C-C片段的对映选择性合成。关键步骤包括高度非对映选择性烯丙基化、由高烯丙醇衍生的丙烯酸酯的闭环烯烃复分解反应、立体选择性端基异构烷基化以及通过朱利亚烯烃化反应构建亚甲基单元。
相似文献
1
An enantioselective synthesis of the C-C segment of antitumor macrolide laulimalide.
Tetrahedron Lett. 2000 Apr 1;41(14):2319-2322. doi: 10.1016/S0040-4039(00)00158-1. Epub 2002 Aug 2.
2
Total synthesis of microtubule-stabilizing agent (-)-laulimalide.
J Org Chem. 2001 Dec 28;66(26):8973-82. doi: 10.1021/jo010854h.
3
Synthetic studies of antitumor macrolide laulimalide: a stereoselective synthesis of the C-C segment.
Tetrahedron Lett. 2000 Jun 10;41(24):4705-4708. doi: 10.1016/S0040-4039(00)00715-2. Epub 2000 Jun 22.
4
An enantioselective synthesis of the C-C segment of antitumor macrolide peloruside A.
Tetrahedron Lett. 2003 May 12;44(20):3967-3969. doi: 10.1016/S0040-4039(03)00744-5. Epub 2003 Apr 24.
5
A stereoselective synthesis of (+)-boronolide.
Tetrahedron Lett. 2000 Feb 12;41(7):1003-1006. doi: 10.1016/S0040-4039(99)02246-7. Epub 2000 Jun 22.
6
Stereoselective synthesis of the C(1)-C(12) segment of iriomoteolide 1a: a very potent macrolide antitumor agent.
Tetrahedron Lett. 2009 Apr 1;50(13):1416-1418. doi: 10.1016/j.tetlet.2009.01.043.
7
Enantioselective total synthesis of (+)-amphidinolide t1.
J Am Chem Soc. 2003 Mar 5;125(9):2374-5. doi: 10.1021/ja021385j.
8
An Intramolecular Case of Sharpless Kinetic Resolution: Total Synthesis of Laulimalide.
Angew Chem Int Ed Engl. 2001 Oct 15;40(20):3842-3846. doi: 10.1002/1521-3773(20011015)40:20<3842::AID-ANIE3842>3.0.CO;2-R.
9
Enantioselective Synthesis of Thailanstatin A Methyl Ester and Evaluation of in Vitro Splicing Inhibition.
J Org Chem. 2018 May 4;83(9):5187-5198. doi: 10.1021/acs.joc.8b00593. Epub 2018 Apr 26.
10
SYNTHETIC STUDIES OF ANTITUMOR MACROLIDE LAULIMALIDE: ENANTIOSELECTIVE SYNTHESIS OF THE C-C SEGMENT BY A CATALYTIC HETERO DIELS-ALDER STRATEGY.
Tetrahedron Lett. 1997 Apr 7;38(14):2427-2430. doi: 10.1016/S0040-4039(97)00416-4. Epub 2000 Mar 17.
引用本文的文献
1
A macrolactonization-based strategy to obtain microtuble-stabilizing agent (-)-laulimalide.
Tetrahedron Lett. 2001 May 14;42(20):3399-3401. doi: 10.1016/S0040-4039(01)00436-1. Epub 2001 Apr 25.
2
Synthetic studies of antitumor macrolide laulimalide: a stereoselective synthesis of the C-C segment.
Tetrahedron Lett. 2000 Jun 10;41(24):4705-4708. doi: 10.1016/S0040-4039(00)00715-2. Epub 2000 Jun 22.
3
Total Synthesis of (-)-Laulimalide.
J Am Chem Soc. 2000 Nov 8;122(44):11027-11028. doi: 10.1021/ja0027416. Epub 2000 Oct 21.
4
Achmatowicz Reaction and its Application in the Syntheses of Bioactive Molecules.
RSC Adv. 2016;6(112):111564-111598. doi: 10.1039/C6RA22611F. Epub 2016 Nov 24.
5
Enantioselective total synthesis and structural assignment of callyspongiolide.
Org Biomol Chem. 2016 Dec 7;14(48):11357-11370. doi: 10.1039/c6ob02051h.
6
Synthesis of Linear (Z)-α,β-Unsaturated Esters by Catalytic Cross-Metathesis. The Influence of Acetonitrile.
Angew Chem Int Ed Engl. 2016 Oct 10;55(42):13210-13214. doi: 10.1002/anie.201608087.
7
Enantioselective Synthesis of Both Epimers at C-21 in the Proposed Structure of Cytotoxic Macrolide Callyspongiolide.
Org Lett. 2016 Jul 1;18(13):3274-7. doi: 10.1021/acs.orglett.6b01523. Epub 2016 Jun 22.
本文引用的文献
1
RING-CLOSING METATHESIS STRATEGY TO UNSATURATED γ- AND δ-LACTONES: SYNTHESIS OF HYDROXYETHYLENE ISOSTERE FOR PROTEASE INHIBITORS.
Tetrahedron Lett. 1998 Jun 25;39(26):4651-4654. doi: 10.1016/S0040-4039(98)00887-9.
2
A stereoselective synthesis of (-)-tetrahydrolipstatin.
Chem Commun (Camb). 1999;1999(17):1743-1744. doi: 10.1039/A904533C.
3
SYNTHETIC STUDIES OF ANTITUMOR MACROLIDE LAULIMALIDE: ENANTIOSELECTIVE SYNTHESIS OF THE C-C SEGMENT BY A CATALYTIC HETERO DIELS-ALDER STRATEGY.
Tetrahedron Lett. 1997 Apr 7;38(14):2427-2430. doi: 10.1016/S0040-4039(97)00416-4. Epub 2000 Mar 17.
4
General Synthesis of alpha-Acetoxy Ethers from Esters by DIBALH Reduction and Acetylation.
J Org Chem. 1996 Nov 15;61(23):8317-8320. doi: 10.1021/jo961205m.
Zotero 插件