Facile enantiodivergent approach to 5-hydroxy-5,6-dihydro-2(1H)-pyridones.: First total synthesis of both enantiomers of pipermethystine

被引：33
|
作者：
Arrayás, RG [1 ]
Alcudia, A [1 ]
Liebeskind, LS [1 ]
机构：
[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA
来源：
ORGANIC LETTERS | 2001年 / 3卷 / 21期
关键词：
D O I：
10.1021/ol010183+
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] A novel enantiodivergent approach to 5-hydroxy-5,6-dihydro-2(lh)-pyridones using a ring closing metathesis and a lipase-mediated kinetic resolution as key steps is described and applied to the first synthesis of both enantiomers of pipermethystine.
引用
收藏
页码：3381 / 3383
页数：3
相关论文
共 50 条
  • [41] An Efficient and Facile Multicomponent Reaction for the Synthesis of 5,6-dihydro-6-hydroxy-6-(trifluoromethyl)-1H-spiro[indoline-3,4-pyrimidine]-2,2(3H)-dione Derivatives under Solvent-Free Conditions
    Xu, Hui
    Yan, Lirong
    Qin, Yaqi
    Xu, Zhongyun
    Ling, Zhi
    Rong, Liangce
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (04) : 2493 - 2500
  • [42] Stereoselective Total Synthesis of (6S)-5,6-Dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one from L-Malic Acid
    Chandrakanth, Dandekar
    Rao, Yerragorla Gopala
    Swamy, Tallapally
    Biradar, Dhanraj
    Vishnupriya, Lonavath
    Reddy, Basi V. Subba
    NATURAL PRODUCT COMMUNICATIONS, 2018, 13 (07) : 867 - 868
  • [43] An asymmetric synthesis of (R)-5-(methylamino)-5,6-dihydro-4H-imidazo-[4,5,1-ij] quinolin-2(1H)-one (1) and its [2-C-14]- and [6,7-H-3(2)]-labeled forms.
    Heier, RF
    Moon, MW
    Stolle, WT
    Easter, JA
    Hsi, RSP
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1996, 38 (12): : 1087 - 1098
  • [44] Diastereoselective and Efficient Synthesis of Indeno[2",1":4′,5′]furo[3′,2′:5,6]pyrido[2,3-d]pyrimidine-2,4,6(1H,3H)-trione and 6-(2,3-Dihydro-2-hydroxy-1,3-dioxo-1H-inden-2-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-2,4,7(1H,3H,6H)-trione Derivatives
    Saberi, Dariush
    Mohammadizadeh, Mohammad Reza
    Esmaeili, Reza
    HELVETICA CHIMICA ACTA, 2015, 98 (10) : 1411 - 1418
  • [45] STUDIES ON POSITIVE INOTROPIC AGENTS .4. SYNTHESIS OF 5-(3-AMINO-2-HYDROXYPROPOXY)-3,4-DIHYDRO-8-HYDROXY-2(1H)-QUINOLINONE DERIVATIVES
    TOMINAGA, M
    OGAWA, H
    YO, E
    YAMASHITA, S
    YABUUCHI, Y
    NAKAGAWA, K
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1987, 35 (09) : 3699 - 3704
  • [46] Stereoselective total synthesis of a potent natural antifungal compound (6S)-5,6,dihydro-6-[(2R)-2-hydroxy-6-phenyl hexyl]-2H-pyran-2-one
    Das, Biswanath
    Laxminarayana, Keetha
    Krishnaiah, Martha
    Kumar, Duddukuri Nandan
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (22) : 6396 - 6398
  • [47] A facile approach to the synthesis of 3,4-dihydro-2H-benzo[4,5]imidazo[2,1-b][1,3,4]thiadiazines
    Khodykina, Evgeniya
    Pobedinskaya, Diana
    Borodkina, Inna
    Astakhov, Alexander
    Demidov, Oleg
    Metelitsa, Anatoly
    Chernyshev, Victor
    Kolodina, Alexandra
    JOURNAL OF SULFUR CHEMISTRY, 2024, 45 (06) : 917 - 940
  • [48] Ethyl 3-(2,4-dioxocyclohexyl)propanoate as a novel precursor for N-substituted 4,4a,5,6-tetrahydroquinoline-2,7(1H,3H)-diones and their corresponding 3,4-dihydro-7-hydroxyquinolin-2(1H)-ones and 7-hydroxyquinolin-2(1H)-ones synthesis
    Vandna Thakur
    Dharminder Sharma
    Pralay Das
    Molecular Diversity, 2016, 20 : 29 - 40
  • [49] Ethyl 3-(2,4-dioxocyclohexyl)propanoate as a novel precursor for N-substituted 4,4a,5,6-tetrahydroquinoline-2,7(1H,3H)-diones and their corresponding 3,4-dihydro-7-hydroxyquinolin-2(1H)-ones and 7-hydroxyquinolin-2(1H)-ones synthesis
    Thakur, Vandna
    Sharma, Dharminder
    Das, Pralay
    MOLECULAR DIVERSITY, 2016, 20 (01) : 29 - 40
  • [50] A facile synthesis of 2-benzoyl-6-hydroxy-3-methyl-5-(2-substituted-2,3-dihydro-1H-1,5-benzodiazepin-4-yl) benzo[b]furans
    Reddy, KVV
    Rao, PS
    Ashok, D
    SYNTHETIC COMMUNICATIONS, 2000, 30 (10) : 1825 - 1836
12345