Stereocontrolled Synthesis of C1-C17 Fragment of Narasin via a Free Radical-Based Approach

被引:17
作者
Brazeau, Jean-Francois
Guilbault, Audrey-Anne
Kochuparampil, Jummey
Mochirian, Philippe
Guindon, Yvan [1 ]
机构
[1] Inst Rech Clin Montreal, Montreal, PQ H2W 1R7, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
ALDOL REACTIONS; ALDEHYDES; STRATEGY; ASSEMBLAGE; MUKAIYAMA; ALCOHOLS; MOTIFS;
D O I
10.1021/ol902414u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of the C1-C17 western unit of narasin was achieved from (S)-Roche ester. Highlights in our synthesis include the successful exploitation of three stereoselective sequences of Lewis acid mediated reaction followed by free-radical-based hydrogen transfer.
引用
收藏
页码:36 / 39
页数:4
相关论文
共 26 条
[1]  
[Anonymous], FRONTIERS CHEM
[2]   Stereopentads Derived from a Sequence of Mukaiyama Aldolization and Free Radical Reduction on α-Methyl-β-alkoxy Aldehydes: A General Strategy for Efficient Polypropionate Synthesis [J].
Brazeau, Jean-Francois ;
Mochrian, Philippe ;
Prevost, Michel ;
Guindon, Yvan .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (01) :64-74
[3]   Phenylselenoethers as precursors of acyclic free radicals. Creating tertiary and quaternary centers using free radical-based intermediates [J].
Cardinal-David, Benoit ;
Brazeau, Jean-Francois ;
Katsoulis, Ioannis A. ;
Guindon, Yvan .
CURRENT ORGANIC CHEMISTRY, 2006, 10 (15) :1939-1961
[4]   TOTAL SYNTHESIS OF LEUKOTRIENE-B5 [J].
COREY, EJ ;
PYNE, SG ;
SU, W .
TETRAHEDRON LETTERS, 1983, 24 (45) :4883-4886
[5]  
DESLONGSCHAMPS P, 1983, STEREOELECTRONIC EFF
[6]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[7]   DOUBLE STEREODIFFERENTIATING ALDOL REACTIONS - THE DOCUMENTATION OF PARTIALLY MATCHED ALDOL BOND CONSTRUCTIONS IN THE ASSEMBLAGE OF POLYPROPIONATE SYSTEMS [J].
EVANS, DA ;
DART, MJ ;
DUFFY, JL ;
RIEGER, DL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (35) :9073-9074
[8]   STEREOSELECTIVE ALDOL REACTIONS OF CHLOROTITANIUM ENOLATES - AN EFFICIENT METHOD FOR THE ASSEMBLAGE OF POLYPROPIONATE-RELATED SYNTHONS [J].
EVANS, DA ;
RIEGER, DL ;
BILODEAU, MT ;
URPI, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :1047-1049
[9]   Strategy and methodology development for the total synthesis of polyether ionophore antibiotics [J].
Faul, MM ;
Huff, BE .
CHEMICAL REVIEWS, 2000, 100 (06) :2407-2473
[10]   Diastereoselective mukaiyama and free radical processes for the synthesis of polypropionate units [J].
Guindon, Y ;
Brazeau, JF .
ORGANIC LETTERS, 2004, 6 (15) :2599-2602