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化学进展 2010, Vol. 22 Issue (01): 58-70 前一篇   后一篇

• 综述与评论 •

过渡金属催化的呋喃合成*

卢玉华1;宋飞杰2;贾学顺1**;刘元红2**   

  1. (1上海大学化学系 上海 200444; 2 中国科学院上海有机化学研究所金属有机化学国家重点实验室 上海 200032)
  • 收稿日期:2009-02-06 修回日期:2009-03-05 出版日期:2010-01-24 发布日期:2010-01-07
  • 通讯作者: 贾学顺;刘元红 E-mail:xsjia@mail.shu.edu.cn;yhliu@mail.sioc.ac.cn
  • 基金资助:

    国家自然科学基金

Transition Metal-Catalyzed Synthesis of Furan Derivatives

Lu Yuhua1; Song Feijie2; Jia Xueshun1**; Liu Yuanhong2**   

  1. (1. Department of Chemistry, Shanghai University, Shanghai 200444, China; 2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China)
  • Received:2009-02-06 Revised:2009-03-05 Online:2010-01-24 Published:2010-01-07
  • Contact: Jia Xueshun;Liu Yuanhong E-mail:xsjia@mail.shu.edu.cn;yhliu@mail.sioc.ac.cn
  • Supported by:

    National Natural Science Foundation of China

呋喃是一类重要的杂环化合物,该类化合物不仅是许多天然产物的核心结构单元,而且大多具有生物活性,在医药、农药以及生物化学方面有着广泛的应用。本文综述了由过渡金属催化的以非环化合物为前体的呋喃衍生物合成的最新研究进展。重点阐述了以联烯酮、炔酮、(Z)-2-烯-4-炔-1-醇(酮)、炔基环氧化物、2-(1-炔基)-2-烯-1-酮这5类化合物为前体的呋喃合成方法,概述了其他一些具有代表性的方法,并展望了呋喃衍生物合成的研究和发展方向。

The furan rings constitute an important class of heterocycles, which behave not only as key structural subunits in numerous natural products, but also display wide range of bioactivities. They also have applications in medicine, agricultural chemicals and biological chemistry. This review focuses on the recent progress in transition metal-catalyzed synthesis of furan derivatives from acyclic precursors such as allenyl ketones, alkynones, (Z)-2-en-4-yn-1-ols (or -ones), alkynyl epoxides, 2-(1-alkynyl)-2-alken-1-ones. The research trend for the synthesis of furan derivatives is also prospected.

Contents
1 Introduction
2 Metal-catalyzed synthesis of furans
2.1 From allenyl ketones
2.2 From alkynones
2.3 From (Z)-2-en-4-yn-1-ols (or -ones)
2.4 From alkynyl epoxides
2.5 From 2-(1-alkynyl)-2-alkene-1-ones
2.6 Other methods
3 Conclusion and prospectives

中图分类号: 

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[ 1 ]  Heaney H, Ahn J S. Comp rehensive Heterocyclic Chemistry II( Eds. KatritzkyA R, Rees CW, Scriven E F V) , Oxford: Pergamon Press, 1996. Vol. 2, 297—436
[ 2 ]  Kênig B. Science of Synthesis, Houben-Weyl Methods of Molecular Transformations ( Eds. Maas G) , Stuttgart, New York: Thieme, 2001. Vol. 9, 183—285
[ 3 ]  The Chemistry of Heterocycles: Structure, Reactions, Syntheses,and Applications ( Eds. Eicher T, Haup tmann S) , Weinheim:Wiley-VCH, 2003. 52—62
[ 4 ]  ElbandyM, Shinde P B, Dang H T, Hong J, Bae K S, Jung J H. J. Nat. Prod. , 2008, 71: 869—872
[ 5 ]  Jadulco R, Proksch P, Wray V, Sudarsono B A, Gr? fe U. J.Nat. Prod. , 2001, 64: 527—530
[ 6 ]  焦耳J A ( Joule J A) , 米尔斯K (Mills K)著. 由业诚(You Y C) , 高大彬(Gao D B) 等译. 杂环化学(Heterocyclic Chemistry) . 北京: 科学出版社(Beijing: Science Press) , 2004.335—361
[ 7 ]  Lip shutz B H. Chem. Rev. , 1986, 86: 795—819
[ 8 ]  MaierM. Organic Synthesis Highlights II ( Eds. Waldmann H) ,VCH: Weinheim, 1995. 231—242
[ 9 ]  Benassi R. Comp rehensive Heterocyclic Chemistry II ( Eds. Katritzky A R, Rees C W, Scriven E F V ) . Oxford: Pergamon Press, 1996, Vol. 2, 259—295
[ 10 ]  Gilchrist T L. J. Chem. Soc. Perkin Trans. 1, 1999,2849—2866
[ 11 ]  Keay B A. Chem. Soc. Rev. , 1999, 28: 209—215
[ 12 ]  Hou X L, Cheung H Y, Hon T Y, Kwan P L, Lo T H, Tong S Y, Wong H N C. Tetrahedron, 1998, 54: 1955—2020
[ 13 ]  Lukevics E, Pudova O A. Chemistry of Heterocyclic Compounds,1997, 33: 133—154
[ 14 ]  Friedrishsen W. Comprehensive Heterocyclic Chemistry II ( Eds.Katrizky A R, Rees C W, Scriven E F V ) , Pergamon: New York, 1996. Vol. 2, 351—393
[ 15 ]  李林涛(Li L T) , 麻生明(Ma S M) . 有机化学(Organic Chemistry) , 2000, 20: 701—711
[ 16 ]  Brown R C D. Angew. Chem. Int. Ed. , 2005, 44: 850—852
[ 17 ]  Marshall J A, Robinson E D. J. Org. Chem. , 1990, 55:3450—3451
[ 18 ]  Marshall J A, Wang X J. J. Org. Chem. , 1991, 56: 960—969
[ 19 ]  Marshall J A, Bartley G S. J. Org. Chem. , 1994, 59: 7169—7171
[ 20 ]  Marshall J A, Sehon C A. J. Org. Chem. , 1995, 60:5966—5968
[ 21 ]  Hashmi A S K. Angew. Chem. Int. Ed. , 1995, 34:1581—1583
[ 22 ]  Alcaide B, Almendros P, Campo TM. Eur. J. Org. Chem. ,2007, 72: 2844—2849
[ 23 ]  Ma SM, Zhang J L. Chem. Commun. , 2000, 117—118
[ 24 ]  Ma S M, Zhang J L, Lu L H. Chem. Eur. J. , 2003, 9:2447—2456
[ 25 ]  Ma SM, Li L T. Org. Lett. , 2000, 2: 941—944
[ 26 ]  Ma SM, Yu ZQ. Angew. Chem. Int. Ed. , 2002, 41: 1775—1778
[ 27 ]  Ma SM, Yu Z Q. Chem. Eur. J. , 2004, 10: 2078—2087
[ 28 ]  Ma SM, Gu Z H, Yu ZQ. J. Org. Chem. , 2005, 70: 6291—6294
[ 29 ]  Sromek A W, Rubina M, Gevorgyan V. J. Am. Chem. Soc. ,2005, 127: 10500—10501
[ 30 ]  Kim J T, Kel′in A V, Gevorgyan V. Angew. Chem. Int. Ed. ,2003, 42: 98—101
[ 31 ]  Sromek A W, Kel′in A V, Gevorgyan V. Angew. Chem. Int.Ed. , 2004, 43: 2280—2282
[ 32 ]  Dudnik A S, Gevorgyan V. Angew. Chem. Int. Ed. , 2007,46: 5195—5197
[ 33 ]  Hashmi A S K, Schwarz L, Choi J H, Frost T M. Angew.Chem. Int. Ed. , 2000, 39: 2285—2288
[ 34 ]  Baker R T, Nguyen P, Marder T B, Westcott S A. Angew.Chem. Int. Ed. , 1995, 34: 1336—1338
[ 35 ]  Zhou C Y, Chan P W H, Che C M. Org. Lett. , 2006, 8:325—328
[ 36 ]  Peng L L, Zhang X, Ma M, Wang J B. Angew. Chem. Int.Ed. , 2007, 46: 1905—1908
[ 37 ]  Fukuda Y, Shiragami H, Utimoto K, Nozaki H. J. Org.Chem. , 1991, 56: 5816—5819
[ 38 ]  Sheng H Y, Lin S Y, Huang Y Z. Synthesis, 1987,1022—1023
[ 39 ]  Sniady A, Durharn A, MorrealeM S, Wheeler K A, Dembinski R. Org. Lett. , 2007, 9: 1175—1178
[ 40 ]  Kel′in A V, Gevorgyan V. J. Org. Chem. , 2002, 67: 95—98
[ 41 ]  Sheng H Y, Lin S Y, Hung Y Z. Tetrahedron Lett. , 1986, 27:4893—4894
[ 42 ]  Dudnik A S, Sromek A W, Rubina M, Kim J T, Kel′in A V,Gevorgyan V. J. Am. Chem. Soc. , 2008, 130: 1440—1452
[ 43 ]  Cadierno V, Gimeno J, Nebra N. Adv. Synth. Catal. , 2007,349: 382—394
[ 44 ]  Zhan Z P , Wang S P, Cai X B, Liu H J, Yu J L, Cui Y Y.Adv. Synth. Catal. , 2007, 349: 2097—2102
[ 45 ]  Imagawa H, Kurisaki T, Nishizawa M. Org. Lett. , 2004, 6:3679—3681
[ 46 ]  Végh D, Zalup sky P, Kováˇc J. Synth. Commun. , 1990, 20:1113—1123
[ 47 ]  Seiller B, Bruneau C, Dixneuf P H J. J. Chem. Soc. Chem.Commun. , 1994, 493—494
[ 48 ]  Seiller B, Bruneau C, Dixneuf P H. Tetrahedron, 1995, 51 :13089—13102
[ 49 ]  Kücükbay H, Cetinkaya B, Guesmi S, Dixneuf P H. Organometallics, 1996, 15: 2434—2439
[ 50 ]  Gabriele B, Salerno G, Lauria E. J. Org. Chem. , 1999, 64:7687—7692
[ 51 ]  Liu Y H, Song F J, Song Z Q, Liu M N, Yan B. Org. Lett. ,2005, 7: 5409—5412
[ 52 ]  Du X W, Song F, Lu Y, Chen H, Liu Y H. Tetrahedron,2009, 65: 1839—1845
[ 53 ]  Gabriele B, Salerno G, De Pascali F, CostaM, Chiusoli G P. J.Org. Chem. , 1999, 64: 7693—7699
[ 54 ]  Bartolo G, Pierluigi P, Giuseppe S, Raffaella M. Synthesis,2006, 24: 4247—4251
[ 55 ]  Díazlvarez A E, Crochet P, ZablockaM, Duhayon C, Cadierno V, Gimeno J, Majoralc J P. Adv. Synth. Catal. , 2006,348: 1671—1679
[ 56 ]  ; zdemir I, YiˇgitB, μetinkaya B, BlküD, TahirM N, Ar¥c¥C.J. Organomet. Chem. , 2001, 633: 27—32
[ 57 ]  Miki K, Nishino F, Ohe K, Uemura S. J. Am. Chem. Soc. ,2002, 124: 5260—5261
[ 58 ]  Miki K, Yokoi T, Nishino F, Kato Y, Washitake Y, Ohe K,Uemura S. J. Org. Chem. , 2004, 69: 1557—1564.
[ 59 ]  McDonald F E, Schultzlb C C. J. Am. Chem. Soc. , 1994,116: 9363—9364
[ 60 ]  Lo C Y, Guo H Y, Lian J J, Shen F M, Liu R S. J. Org.Chem. , 2002, 67: 3930—3932
[ 61 ]  Aurrecoechea J M, Pérez E, SolayM. J. Org. Chem. , 2001,66 : 564—569
[ 62 ]  Aurrecoechea J M, Pérez E. Tetrahedron, 2004, 60:4139—4149
[ 63 ]  Hashmi A S K, Sinha P. Adv. Synth. Catal. , 2004, 346:432—438
[ 64 ]  Shu X Z, Liu X Y, Xiao H Q, J i K G, Guo L N, Qi C Z, Liang YM. Adv. Synth. Catal. , 2007, 349: 2493—2498
[ 65 ]  J i K G, Shen YW, Shu X Z, Xiao H Q, Bian Y J, Liang YM.Adv. Synth. Catal. , 2008, 350: 1275—1280
[ 66 ]  Yao TL, Zhang X X, Larock R C. J. Am. Chem. Soc. , 2004,126: 11164—11165
[ 67 ]  Patil N T, Wu H, Yamamoto Y. J. Org. Chem. , 2005, 70:4531—4534
[ 68 ]  Oh C H, Reddy V R, Kim A, Rhim C Y. Tetrahedron Lett. ,2006, 47: 5307—5310
[ 69 ]  Liu X Y, Pan Z L, Shu X Z, Duan X H, Liang YM. Synlett,2006, 1962—1964
[ 70 ]  Xiao Y J, Zhang J L. Angew. Chem. Int. Ed. , 2008, 47:1903—1906
[ 71 ]  Zhang J L, Schmalz H. Angew. Chem. Int. Ed. , 2006, 45:6704—6707
[ 72 ]  Duan X H, Liu X Y, Guo L N, LiaoM C, LiuW M, Liang YM. J. Org. Chem. , 2005, 70: 6980—6983
[ 73 ]  Karpov A S, Merkul E, Oeser T, Müller T J J. Chem. Commun. , 2005, 2581—2583
[ 74 ]  SuhreM H, ReifM, Kirsch S F. Org. Lett. , 2005, 7: 3925—3927
[ 75 ]  For aDFT study, see: Correa A, Marion N, Fensterbank L, MalacriaM, Nolan S P, Cavallo L. Angew. Chem. , Int. Ed. ,2008, 47: 718—721
[ 76 ]  Zhang L M, Sun JW, Kozmin SA. Adv. Synth. Catal. , 2006,348: 2271—2296
[ 77 ]  Marco2Contelles J, Soriano E. Chem. Eur. J. , 2007, 13:1350—1357
[ 78 ]  Marion N, Nolan S P. Angew. Chem. Int. Ed. , 2007, 46:2750—2752
[ 79 ]  Fürstner A, Davies P. Angew. Chem. Int. Ed. , 2007, 46:3410—3449
[ 80 ]  Barluenga J, Riesgo L, Vicente R, López L A, TomásM. J.Am. Chem. Soc. , 2008, 130: 13528—13529
[ 81 ]  Ma SM, Zhang J L. J. Am. Chem. Soc. , 2003, 125: 12386—12387
[ 82 ]  Zhan L B, Guan Z H, Han Y, Xie Y X, He S, Liang YM. J.Org. Chem. , 2007, 72: 10276—10278
[ 83 ]  Arcadi A, Cacchi S, Fabrizi G, Marinelli F, Parisi L M. Tetrahedron, 2003, 59: 4661—4671
[ 84 ]  Yadav J S, Reddy B V S, SreenivasM, Satheesh G. Synthesis,2007, 11: 1712—1716
[ 85 ]  Dey S, Nandi D, Pradhan P K, Giri V S, Jaisankar P. Tetrahedron Lett. , 2007, 48: 2573—2575
[ 86 ]  Donohoe T J, Orr A J, Gosby K, Bingham M. Eur. J. Org.Chem. , 2005, 1969—1971
[ 87 ]  Donohoe T J, Fishlock L P, Lacy A R, Procop iou P A. Org.Lett. , 2007, 9: 953—956
[ 88 ]  Leclerc E, Tius M A. Org. Lett. , 2003, 5: 1171—1174
[ 89 ]  Hashmi A S K, Schwarz L, Bolte M. Eur. J. Org. Chem. ,2004, 1923—1935
[ 90 ]  Hayes S J, KnightD W, MenziesM D, O’HalloranM, TanW F. Tetrahedron Lett. , 2007, 48: 7709—7712
[ 91 ]  Oh C H, Park H M, Park D I. Org. Lett. , 2007, 9:1191—1193
[ 92 ]  Zhang D, Yuan C. Eur. J. Org. Chem. , 2007, 3916—3924

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摘要

过渡金属催化的呋喃合成*