Furans and singlet oxygen - why there is more to come from this powerful partnership

被引:115
作者
Montagnon, Tamsyn [1 ]
Kalaitzakis, Dimitris [1 ]
Triantafyllakis, Myron [1 ]
Stratakis, Manolis [1 ]
Vassilikogiannakis, Georgios [1 ]
机构
[1] Univ Crete, Dept Chem, Iraklion 71003, Crete, Greece
基金
欧洲研究理事会;
关键词
BIOMIMETIC TOTAL-SYNTHESIS; ONE-POT SYNTHESIS; DYE-SENSITIZED PHOTOOXYGENATION; RACEMIC BICYCLIC LACTAMS; DIELS-ALDER REACTIONS; PHOTOSENSITIZED OXIDATION; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; GAMMA-HYDROXYBUTENOLIDES;
D O I
10.1039/c4cc02083a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The purpose of this article is to give a taste of just how powerful the union between furans and photochemically-generated singlet oxygen is proving to be as a synthetic tool and to suggest that this chemistry is only now really coming of age. In attempting to achieve this goal, its progress from mechanistic curiosity to rapidly maturing applied science will be followed. It will be shown how the field has reached a point where the diversity of product structures attainable is expanding all the time at a tremendous pace and how this expansion allows for a wide variety of important developments from the discovery of new materials and methods for DNA-crosslinking, to the delineation of more sustainable synthetic technologies. To begin with, however, we look briefly at the investigations of the pioneers who laid all the necessary foundations by unravelling the reactions' key characteristics and then we will move on to show how their crucial work has been exploited and applied in increasingly creative ways over the years that have followed.
引用
收藏
页码:15480 / 15498
页数:19
相关论文
共 217 条
[21]  
Breitmaier E., 2006, TERPENES FLAVOURS FR, P24, DOI 10.1002/9783527609949. ch1
[22]   Synthesis of bis-spiroacetal ring systems [J].
Brimble, MA ;
Farès, FA .
TETRAHEDRON, 1999, 55 (25) :7661-7706
[23]   Developments in furan syntheses [J].
Brown, RCD .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (06) :850-852
[24]  
BROWN RCD, 1994, SYNLETT, P417
[25]   Redox Economy in Organic Synthesis [J].
Burns, Noah Z. ;
Baran, Phil S. ;
Hoffmann, Reinhard W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (16) :2854-2867
[26]   2 SYNTHESES OF MANOALIDE VIA HETEROATOM-ASSISTED ALKYNE CARBOMETALLATION [J].
BURY, P ;
HAREAU, G ;
KOCIENSKI, P ;
DHANAK, D .
TETRAHEDRON, 1994, 50 (29) :8793-8808
[27]   Tandem Suzuki-Miyaura Coupling/Acid-Catalyzed Cyclization between Vinyl Ether Boronates and Vinyl Halides: A Concise Approach to Polysubstituted Furans [J].
Butkevich, Alexey N. ;
Meerpoel, Lieven ;
Stansfield, Ian ;
Angibaud, Patrick ;
Corbu, Andrei ;
Cossy, Janine .
ORGANIC LETTERS, 2013, 15 (15) :3840-3843
[28]   Microphotochemistry Using 5-mm Light-Emitting Diodes: Energy-Efficient Photooxidations [J].
Carney, John M. ;
Hammer, Reagan J. ;
Hulce, Martin ;
Lomas, Chad M. ;
Miyashiro, Dayna .
SYNTHESIS-STUTTGART, 2012, 44 (16) :2560-2566
[29]   A mildly inducible and selective cross-link methodology for RNA duplexes [J].
Carrette, L. L. G. ;
Gyssels, E. ;
Loncke, J. ;
Madder, A. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (06) :931-935
[30]   METABOLITES OF THE NUDIBRANCH CHROMODORIS-FUNEREA AND THE SINGLET OXYGEN OXIDATION-PRODUCTS OF FURODYSIN AND FURODYSININ [J].
CARTE, B ;
KERNAN, MR ;
BARRABEE, EB ;
FAULKNER, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (18) :3528-3532