Stereoselective synthesis of 1,3-diols

被引:161
作者
Bode, SE
Wolberg, M
Müller, M
机构
[1] Univ Freiburg, Inst Pharmaceut Sci, Dept Pharmaceut & Med Chem, D-79104 Freiburg, Germany
[2] DSM Pharma Chem GmbH, D-93055 Regensburg, Germany
来源
SYNTHESIS-STUTTGART | 2006年 / 04期
关键词
asymmetric synthesis; reductions; aldol reactions; biocatalysis; desymmetrizations; alcohols;
D O I
10.1055/s-2006-926315
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Many polyketide-derived natural products contain a synor anti-1,3-diol unit. No general and simple approach exists for the flexible synthesis of polyols and other polyketide-derived structural units, therefore a multitude of methods for the stereoselective synthesis of 1,3-diols has been developed. Asymmetric homogeneous and heterogeneous hydrogenation and diastereoselective reduction, chain elongation, enzymatic and nonenzymatic desymmetrization, or dynamic kinetic resolution are some of these methods. The development of different methods to synthesize these 1,3-diols stereoselectively is important, as often small structural changes in a molecule result in low yields or low stereoselectivity with a known method. This review article highlights some of the recent developments in this field.
引用
收藏
页码:557 / 588
页数:32
相关论文
共 324 条
[1]  
ADAMS DR, 1977, SYNTHESIS-STUTTGART, P661
[2]   Stereospecific conversion of (1R*,3S*)- and (1R*,3R*)-3-cyclohexyl-1-phenylpropane-1,3-diol into the corresponding 2,4-disubstituted oxetanes [J].
Aftab, T ;
Carter, C ;
Christlieb, M ;
Hart, J ;
Nelson, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (05) :711-722
[3]   Reductions of 1,3-dicarbonyl systems with ruthenium-biarylbisphosphine catalysts [J].
Ager, DJ ;
Laneman, SA .
TETRAHEDRON-ASYMMETRY, 1997, 8 (20) :3327-3355
[4]  
[Anonymous], 2003, ANGEW CHEM
[5]  
[Anonymous], 2004, ANGEW CHEM
[6]  
[Anonymous], 2005, ANGEW CHEM, V117, P960
[7]   INTRAMOLECULAR HYDROSILYLATIONS .2. THE ANTI-SELECTIVE REDUCTION OF BETA-HYDROXYKETONES [J].
ANWAR, S ;
DAVIS, AP .
TETRAHEDRON, 1988, 44 (13) :3761-3770
[8]   A VERY SIMPLE SYNTHESIS OF NATURAL SATURATED DELTA-SUBSTITUTED DELTA-ACTONES - THE PHEROMONE OF VESPA-ORIENTALIS [J].
BACARDIT, R ;
MORENOMANAS, M .
CHEMISTRY LETTERS, 1982, (01) :5-6
[9]   MEERWEIN PONNDORF VERLEY REACTION OF ALPHA-KETOEPOXIDES - A STEREOCONTROLLED ONE-STEP SYNTHESIS OF EPOXY-1,3-DIOL MONOESTERS [J].
BARAMEE, A ;
CHAICHIT, N ;
INTAWEE, P ;
THEBTARANONTH, C ;
THEBTARANONTH, Y .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (15) :1016-1017
[10]   CARBONATE EXTENSION - A VERSATILE PROCEDURE FOR FUNCTIONALIZATION OF ACYCLIC HOMOALLYLIC ALCOHOLS WITH MODERATE STEREOCONTROL [J].
BARTLETT, PA ;
MEADOWS, JD ;
BROWN, EG ;
MORIMOTO, A ;
JERNSTEDT, KK .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (21) :4013-4018