Oxazolidinones as chiral auxiliaries in asymmetric aldol reactions applied to total synthesis

被引:165
作者
Heravi, Majid M. [1 ]
Zadsirjan, Vahideh [1 ]
机构
[1] Alzahra Univ, Sch Sci, Dept Chem, Tehran, Iran
关键词
STEREOSELECTIVE TOTAL-SYNTHESIS; CYTOTOXIC 35-MEMBERED CYCLODEPSIPEPTIDES; CYANOBACTERIUM LYNGBYA-MAJUSCULA; ICHTHYOTOXIC CYCLIC LIPOPEPTIDE; DINOFLAGELLATE AMPHIDINIUM SP; ALDER CYCLOADDITION REACTIONS; DIARRHETIC SHELLFISH TOXINS; SPONGE DYSIDEA-ARENARIA; MICROSCLERODERMINS F-I; FORMAL TOTAL SYNTHESIS;
D O I
10.1016/j.tetasy.2013.08.011
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Asymmetric aldol reactions of oxazolidinones as chiral auxiliaries have been achieved and attracted significant consideration as one of the most powerful synthetic tools for the carbon-carbon bond-forming reactions. The methodology has been highly successful in the stereoselective construction of a number of natural products, antibiotics, and other medicinally important compounds. The present review is focused on the utility and versatility of oxazolidinones (Evans chiral auxiliaries) in the asymmetric aldol condensations for the total synthesis of natural products and complex targets. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1149 / 1188
页数:40
相关论文
共 196 条
[1]  
ACHENBAC.H, 1970, TETRAHEDRON LETT, P3259
[2]   1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].
Ager, DJ ;
Prakash, I ;
Schaad, DR .
CHEMICAL REVIEWS, 1996, 96 (02) :835-875
[3]  
Ager DJ, 1997, ALDRICHIM ACTA, V30, P3
[4]   Stereoselective synthesis of the octahydroisobenzofuran skeleton of the eunicellins [J].
Akindele, T ;
Marsden, SP ;
Cumming, JG .
TETRAHEDRON LETTERS, 2005, 46 (42) :7235-7238
[5]   Highly effective and recyclable chiral auxiliaries: a study of the synthesis and use of three 4-isopropyl-5,5-diaryloxazolidin-2-ones [J].
Alexander, K ;
Cook, S ;
Gibson, CL ;
Kennedy, AR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (13) :1538-1549
[6]   Total synthesis of ulongamide A, a cyclic depsipeptide isolated from marine cyanobacteria Lyngbya sp. [J].
Alvarado, Cuauhtemoc ;
Diaz, Eduardo ;
Guzman, Angel .
TETRAHEDRON LETTERS, 2007, 48 (04) :603-607
[7]   Inhibition of IkB kinase and NF-κB by a novel synthetic compound SK 2009 [J].
Anchoori, Ravi Kumar ;
Harikumar, Kuzhuvelil B. ;
Batchu, Venkateswara Rao ;
Aggarwal, Bharat B. ;
Khan, Saeed R. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (01) :229-235
[8]   Synthesis of the C1-side chain of zaragozic acid D and progress towards a total synthesis [J].
Armstrong, A ;
Barsanti, PA ;
Blench, TJ ;
Ogilvie, R .
TETRAHEDRON, 2003, 59 (03) :367-375
[9]   Advances in asymmetric enolate methodology [J].
Arya, P ;
Qin, HP .
TETRAHEDRON, 2000, 56 (07) :917-947
[10]  
Bailey S. C., 1995, BIOL MED CHEM, V5, P2483