Recent Advances in the Synthesis of Natural 2-Deoxy-β-glycosides

被引:83
作者
Borovika, Alina [1 ]
Nagorny, Pavel [1 ]
机构
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
关键词
2-deoxy-beta-glycosides; Glycosylation; Synthesis; Natural products; PALLADIUM-CATALYZED GLYCOSYLATION; GLYCOSIDE BOND SYNTHESIS; DE-NOVO SYNTHESIS; HIGHLY STEREOSELECTIVE-SYNTHESIS; CHAPERONE DOWN-REGULATOR; BETA-D-MANNOPYRANOSIDES; LANDOMYCIN-A; GOLD(I)-CATALYZED GLYCOSYLATION; ORTHO-ALKYNYLBENZOATES; STEREOCONTROLLED SYNTHESIS;
D O I
10.1080/07328303.2012.663432
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
This report provides an overview of the recent synthetic efforts directed toward the assembly of complex 2-deoxy-beta-glycoside-containing natural products landomycin A, apoptolidin A, digitoxin, lomaiviticin A, incednine, and versipelostatin. In particular, the intention of this review is to cover the work published since the earlier reports on this topic by Lowary and Hou (2009) and Franck and Marzabadi (2000).
引用
收藏
页码:255 / 283
页数:29
相关论文
共 133 条
[71]   Assembly of Digitoxin by Gold(I)-Catalyzed Glycosidation of Glycosyl o-Alkynylbenzoates [J].
Ma, Yuyong ;
Li, Zhongzhen ;
Shi, Hefang ;
Zhang, Jian ;
Yu, Biao .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (23) :9748-9756
[72]   The synthesis of 2-deoxyglycosides: 1988-1999 [J].
Marzabadi, CH ;
Franck, RW .
TETRAHEDRON, 2000, 56 (43) :8385-8417
[73]  
McCombie S. W., 1975, J CHEM SOC P1, V1, P1574
[74]   Stereoselective glycosylations of a family of 6-deoxy-1,2-glycals generated by catalytic alkynol cycloisomerization [J].
McDonald, FE ;
Reddy, KS ;
Díaz, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (18) :4304-4309
[75]  
McDonald FE, 2001, ANGEW CHEM INT EDIT, V40, P3653, DOI 10.1002/1521-3773(20011001)40:19<3653::AID-ANIE3653>3.0.CO
[76]  
2-W
[77]   Discovery of the tungsten carbonyl-catalyzed endo-selective alkynyl alcohol cycloisomerization reaction:: applications to stereoselective syntheses of D-olivose, D-olivose disaccharide substructures of landomycin and mithramycin [J].
McDonald, FE ;
Reddy, KS .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 617 (01) :444-452
[78]   Altering the glycosylation pattern of bioactive compounds [J].
Méndez, C ;
Salas, JA .
TRENDS IN BIOTECHNOLOGY, 2001, 19 (11) :449-456
[79]   Stereoselective Synthesis of 2-Deoxy-β-glycosides Using Anomeric O-Alkylation/Arylation [J].
Morris, William J. ;
Shair, Matthew D. .
ORGANIC LETTERS, 2009, 11 (01) :9-12
[80]   New and stereospecific synthesis of allenes in a single step from propargylic alcohols [J].
Myers, AG ;
Zheng, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (18) :4492-4493