Synthesis of the β2 agonist (R)-salmeterol using a sequence of supported reagents and scavenging agents

被引:26
作者
Bream, RN
Ley, SV
Procopiou, PA
机构
[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England
[2] GlaxoSmithKline Res & Dev Ltd, Med Res Ctr, Stevenage SG1 2NY, Herts, England
基金
加拿大自然科学与工程研究理事会; 中国国家自然科学基金;
关键词
D O I
10.1021/ol020128g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
graphic The enantioselective synthesis of (R)-salmeterol has been achieved by using a sequence of supported reagents and sequestering agents. The saligenin core was installed by a regiospecific alkylation and a chiral auxiliary approach was employed to introduce the desired stereochemistry via a diastereoselective reduction.
引用
收藏
页码:3793 / 3796
页数:4
相关论文
共 23 条
[1]   Polymer-supported reagents for multi-step organic synthesis: Application to the synthesis of sildenafil [J].
Baxendale, IR ;
Ley, SV .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (17) :1983-1986
[2]   Synthesis of nornicotine, nicotine and other functionalised derivatives using solid-supported reagents and scavengers [J].
Baxendale, IR ;
Brusotti, G ;
Matsuoka, M ;
Ley, SV .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (02) :143-154
[3]  
Baxendale IR, 2001, SYNLETT, P1482
[4]  
BREAM RN, UNPUB J CHEM SOC P1
[5]   Polymer-supported catalysis in synthetic organic chemistry [J].
Clapham, B ;
Reger, TS ;
Janda, KD .
TETRAHEDRON, 2001, 57 (22) :4637-4662
[6]  
DEMIGUEL YR, 2002, J CHEM SOC P1, P1857
[7]  
Evans B., 1991, EP-A, Patent No. 422889
[8]   Synthesis of the potent analgesic compound (±)-epibatidine using an orchestrated multi-step sequence of polymer supported reagents [J].
Habermann, J ;
Ley, SV ;
Scott, JS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (10) :1253-1255
[9]   ENANTIOSELECTIVE SYNTHESIS OF SALMETEROL VIA ASYMMETRIC BORANE REDUCTION [J].
HETT, R ;
STARE, R ;
HELQUIST, P .
TETRAHEDRON LETTERS, 1994, 35 (50) :9375-9378
[10]   CONVERSION OF ALCOHOLS INTO ALKYL BROMIDES USING POLYMER-SUPPORTED TRIPHENYLPHOSPHINE DIBROMIDE AND POLYMER-SUPPORTED TRIPHENYLPHOSPHINE AND CARBON TETRABROMIDE [J].
HODGE, P ;
KHOSHDEL, E .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (02) :195-198