A NEW SYNTHETIC STRATEGY FOR 2-DEOXY-D-RIBOSE VIA PALLADIUM(II)-CATALYZED CYCLIZATION OF ALDEHYDE

被引:5
|
作者
Miyazawa, Masahiro [1 ]
Awasaguchi, Ken-ichiro [1 ]
Uoya, Ikuyo [1 ]
Yokoyama, Hajime [1 ]
Hirai, Yoshiro [1 ]
机构
[1] Toyama Univ, Grad Sch Sci & Technol, Toyama 9308555, Japan
关键词
Carbohydrate; Hemiacetal; Tetrahydropyran; Stereoselectivity; Anomeric Effect; STEREOCONTROLLED CYCLIZATION; N-ALKYLATION; CONSTRUCTION; URETHANES; EFFICIENT; AGENTS; ACID;
D O I
10.3987/COM-10-11988
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We achieved a total synthesis of 2-deoxy-D-ribose through intramolecular Pd(II)-catalyzed cyclization of aldehyde via an unstable hemiacetal intermediate as a key step.
引用
收藏
页码:1891 / 1902
页数:12
相关论文
共 50 条
  • [41] Cascade Reactions to Substituted 1 H -Pyrrole-3-carbonitriles via Ligand-Free Palladium(II)-Catalyzed C(sp)-C(sp 2 ) Coupling
    Wang, Zijuan
    Chen, Wenteng
    Luo, Haofan
    He, Chang
    Zhang, Guolin
    Yu, Yongping
    SYNTHESIS-STUTTGART, 2020, 52 (11): : 1659 - 1665
  • [42] Additive-Controlled Divergent Synthesis of Indole and 4H-Benzo[d][1,3]oxazine Derivatives: Palladium-Catalyzed Carbonylative Cyclization of 2-Alkynylanilines and Benzyl Chlorides
    Wang, Qi
    Yao, Lingyun
    Wang, Jian-Shu
    Ying, Jun
    Wu, Xiao-Feng
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (05) : 3874 - 3882
  • [43] Fluoride-Catalyzed Addition of PhSCF2SiMe3 to N-Substituted Cyclic Imides Followed by Radical Cyclization: General Synthetic Strategy of gem-Difluoromethylenated 1-Azabicyclic Compounds
    Bootwicha, Teerawut
    Panichakul, Duanghathai
    Kuhakarn, Chutima
    Prabpai, Samran
    Kongsaeree, Palangpon
    Tuchinda, Patoomratana
    Reutrakul, Vichai
    Pohmakotr, Manat
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10) : 3798 - 3805
  • [44] The Ligand Free Palladium(II)-Catalyzed Regioselective 1,2-Addition of Enol Silanes to Quinones to Access 4-Hydroxy-4-(2-oxo-2-arylethyl)cyclohexadien-1-ones and Synthetic Applications
    Polimera, Subba Rao
    Subbaiah, Murugaiah A. M.
    Ilangovan, Andivelu
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (21) : 14356 - 14370
  • [45] Copper(ii)-catalyzed tandem cyclization for the synthesis of benzo[d][1,3]thiazin-2-yl phosphonates involving C-P and C-S bond formation
    Liu, Yang
    Yao, Shijie
    Wang, Chaoli
    Zhang, Yahui
    Hao, Wenyan
    RSC ADVANCES, 2020, 10 (53) : 32211 - 32215
  • [46] A new route toward 2-acetamido-4-O-methyl-2-deoxy-D-mannopyranose from a Ferrier derivative of tri-O-acetyl-D-glucal, which contributes to aldolase-catalyzed synthesis of laninamivir (CS-8958)
    Okazaki, Hayato
    Hanaya, Kengo
    Shoji, Mitsuru
    Hada, Noriyasu
    Sugai, Takeshi
    TETRAHEDRON, 2013, 69 (37) : 7931 - 7935
  • [47] A Novel Approach to N-Tf 2-Aryl-2,3-Dihydroquinolin-4(1H)-ones via a Ligand-Free Pd(II)-Catalyzed Oxidative Aza-Michael Cyclization
    Kim, Young Min
    Yoo, Hyung-Seok
    Son, Seung Hwan
    Kim, Ga Yeong
    Jang, Hyu Jeong
    Kim, Dong Hwan
    Kim, Soo Dong
    Park, Boyoung Y.
    Kim, Nam-Jung
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (04) : 618 - 622
  • [48] Microwave-Assisted Copper(II)-Catalyzed Cascade Cyclization of 2-Propargylamino/Oxy-Arylaldehydes and O-Phenylenediamines: Access to Densely Functionalized Benzo[f]Imidazo[1,2-d][1,4]Oxazepines and Benzo[f]Imidazo[1,2-d][1,4]Diazepines
    Rajput, Diksha
    Kumar, Atul
    Jandial, Tanvi
    Karuppasamy, Muthu
    Bhuvanesh, Nattamai
    Kumar, Raju Suresh
    Almansour, Abdulrahman I.
    Sridharan, Vellaisamy
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (14) : 8956 - 8969
  • [49] C(sp2)-H Functionalization of Imidazole at the C2-and C4-Position via Palladium-Catalyzed Isocyanide Insertion Leading to Indeno[1,2-d]imidazole and Imidazo[1,2-a]indole Derivatives
    Ren, Zhi-Lin
    Cai, Shuang
    Liu, Ying-Ying
    Xie, Yin-Qing
    Yuan, Ding
    Lei, Min
    He, Ping
    Wang, Long
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (16) : 11014 - 11024
  • [50] One-Pot, Three-Component Synthesis of Novel 4-Phenyl-2-[3-(alkynyl/alkenyl/aryl)phenyl]pyrimidine Libraries via Michael Addition, Cyclization, and C-C Coupling Reactions: A New MCR Strategy
    Reddy, L. Srinivasula
    Reddy, T. Ram
    Reddy, N. C. Gangi
    Mohan, Reddy Bodireddy
    Lingappa, Y.
    SYNTHESIS-STUTTGART, 2013, 45 (01): : 75 - 84