A concise formal synthesis of unnatural (+)-aphanorphine from (2S,4R)-4-hydroxyproline

被引：16
|
作者：
Ma, Zhiqiang
Zhai, Hongbin
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Lab Modern Synthet Organ Chem, Shanghai 200032, Peoples R China
[2] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat Biomimet Drugs, Beijing 100083, Peoples R China
来源：
SYNLETT | 2007年 / 01期
关键词：
aphanorphine; configuration inversion; intramolecular Friedel-Crafts; marine alkaloid; synthesis;
D O I：
10.1055/s-2006-956499
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(-)-Aphanorphine methyl ether was synthesized in ten steps from commercially available (2S,4R)-4-hydroxyproline, featuring the C-2 configuration inversion of an intermediate amide and intramolecular Friedel-Crafts reaction. The present work constitutes a formal synthesis of unnatural (+)-aphanorphine.
引用
收藏
页码：161 / 163
页数：3
相关论文
共 50 条
  • [21] Comparative enzymology of (2S,4R)4-fluoroglutamine and (2S,4R)4-fluoroglutamate
    Cooper, Arthur J. L.
    Krasnikov, Boris F.
    Pinto, John T.
    Kung, Hank F.
    Li, Jianyong
    Ploessl, Karl
    COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY B-BIOCHEMISTRY & MOLECULAR BIOLOGY, 2012, 163 (01): : 108 - 120
  • [22] Synthesis of (2S,4R)-4-aminoethyl-L-Pro and (2S,4R)-4-carboxymethyl-L-Pro from (2S,4R)-Nα-Boc-4-hydroxy-L-Pro methyl ester
    McCafferty, DG
    Schneider, SL
    Erickson, BW
    PEPTIDES FOR THE NEW MILLENNIUM, 2000, : 72 - 73
  • [23] (2S,4R)- and (2S,4S)-Perfluoro-tert-butyl 4-Hydroxyproline: Two Conformationally Distinct Proline Amino Acids for Sensitive Application in 19F NMR
    Tressler, Caitlin M.
    Zondlo, Neal J.
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (12): : 5880 - 5886
  • [24] A convenient and efficient synthesis of (2S,4R)- and (2S,4S)-4-methylglutamic acid
    Coudert, E
    Acher, F
    Azerad, R
    SYNTHESIS-STUTTGART, 1997, (08): : 863 - &
  • [25] Asymmetric synthesis of orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithine
    Lépine, R
    Carbonnelle, AC
    Zhu, JP
    SYNLETT, 2003, (10) : 1455 - 1458
  • [26] Asymmetric synthesis of (2S,4R)-4-hydroxypipecolic acid
    Brooks, CA
    Comins, DL
    TETRAHEDRON LETTERS, 2000, 41 (19) : 3551 - 3553
  • [27] A Convenient and Efficient Synthesis of (2S,4R)- and (2S,4S)-4-Methylglutamic Acid
    Coudert, E.
    Acher, F.
    Azerad, R.
    Synthesis, (08):
  • [28] Stereoselective synthesis of (2S,4R)-4-hydroxypipecolic acid
    Occhiato, Ernesto G.
    Scarpi, Dina
    Guarna, Antonio
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (03) : 524 - 531
  • [29] EFFICIENT SYNTHESIS OF A NEW AMINO-ACID, (2S,3R,4R)-4-CHLORO-3-HYDROXYPROLINE
    LEE, S
    KODERA, Y
    NODA, K
    AOYAGI, H
    KATO, T
    IZUMIYA, N
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (02) : 493 - 495
  • [30] Concise Synthesis of (2R,4R)-Monatin
    Amino, Yusuke
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2016, 64 (08) : 1242 - 1247
12345