Organocatalyzed Protecting-Group-Free Total Synthesis of (S,S)- and (S,R)-Reboxetine, an Antidepressant Drug

被引：2
作者：
Sharma, Ajay [1 ]
Pandey, Satyendra Kumar [1 ]
机构：
[1] Banaras Hindu Univ, Inst Sci, Dept Chem, Varanasi 221005, Uttar Pradesh, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 15期
关键词：
(S; S)-REBOXETINE SUCCINATE; ASYMMETRIC EPOXIDATION; MITSUNOBU REACTION; REBOXETINE; AZODICARBOXYLATE; TRANSFORMATION; DERIVATIVES; CHEMISTRY; ALCOHOLS;
D O I：
10.1021/acs.joc.2c00886
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient, simple, and concise organocatalyzed protecting-group free synthetic approach to the stereoisomers of the antidepressant drug reboxetine and its implementation toward the asymmetric synthesis of (S,S)-reboxetine and (S,R)-reboxetine from commercially available trans-cinnamaldehyde are described. The synthesis features organocatalytic Jorgensen asymmetric epoxidation, epoxide migration, and Mitsunobu inversion as key steps.
引用
收藏
页码：10430 / 10434
页数：5
相关论文
共 34 条
  • [1] Catalyst-Controlled Diastereoselection in the Hydrogenation of Heterocycloalkyl Ketones
    Akashi, Masaya
    Arai, Noriyoshi
    Inoue, Tsutomu
    Ohkuma, Takeshi
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (11-12) : 1955 - 1960
  • [2] The use of environmental metrics to evaluate green chemistry improvements to the synthesis of (S,S)-reboxetine succinate
    Assaf, Georges
    Checksfield, Graham
    Critcher, Doug
    Dunn, Peter J.
    Field, Stuart
    Harris, Laurence J.
    Howard, Roger M.
    Scotney, Gemma
    Scott, Adam
    Mathew, Suju
    Walker, Geoffrey M. H.
    Wilder, Alexander
    [J]. GREEN CHEMISTRY, 2012, 14 (01) : 123 - 129
  • [3] SELECTIVE TRANSFORMATION OF 2,3-EPOXY ALCOHOLS AND RELATED DERIVATIVES - STRATEGIES FOR NUCLEOPHILIC-ATTACK AT CARBON-1
    BEHRENS, CH
    KO, SY
    SHARPLESS, KB
    WALKER, FJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) : 5687 - 5696
  • [4] Efficacy and tolerability of reboxetine compared with imipramine in a double-blind study in patients suffering from major depressive episodes
    Berzewski, H
    VanMoffaert, M
    Gagiano, CA
    [J]. EUROPEAN NEUROPSYCHOPHARMACOLOGY, 1997, 7 : S37 - S47
  • [5] Asymmetric synthesis of (+)-(S,S)-reboxetine via a new (S)-2-(hydroxymethyl)morpholine preparation
    Brenner, E
    Baldwin, RM
    Tamagnan, G
    [J]. ORGANIC LETTERS, 2005, 7 (05) : 937 - 939
  • [6] Regioselective monochloro substitution in carbohydrates and non-sugar alcohols via Mitsunobu reaction: applications in the synthesis of reboxetine
    Dar, Abdul Rouf
    Aga, Mushtaq A.
    Kumar, Brijesh
    Yousuf, Syed Khalid
    Taneja, Subhash Chandra
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (36) : 6195 - 6207
  • [7] Total synthesis of haliclamide
    Gahalawat, Suraksha
    Pandey, Satyendra Kumar
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (39) : 9287 - 9293
  • [8] Total Synthesis of (+)-Petromyroxol, a Marine Natural Product
    Gahalawat, Suraksha
    Garg, Yuvraj
    Pandey, Satyendra Kumar
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (10) : 1025 - 1029
  • [9] Organocatalytic Asymmetric Tandem -Aminooxylation-Henry Reactions for the Synthesis of 1,2-Diols: Total Synthesis of (-)-l-threo-Sphinganine
    Garg, Yuvraj
    Kaur, Ramandeep
    Pandey, Satyendra Kumar
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (45) : 6700 - 6707
  • [10] An Enantioselective Approach to Functionalized Amino Acids: Total Synthesis of Antiepileptic Drug (R)-Lacosamide
    Garg, Yuvraj
    Pandey, Satyendra Kumar
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (08) : 4201 - 4203
1234