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
  • [1] SYNTHESIS OF 2-DEOXY-L-RIBOSE VIA PALLADIUM(II)-CATALYZED CYCLIZATION
    Miyazawa, Masahiro
    Akita, Erika
    Onda, Kazusi
    Narantsetseg, Magsarjav
    Minabe, Haruna
    Yokoyama, Hajime
    Hirai, Yoshiro
    HETEROCYCLES, 2014, 89 (02) : 399 - 412
  • [2] Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalcones via palladium(ii)-catalyzed oxidative cyclization
    Son, Seung Hwan
    Cho, Yang Yil
    Yoo, Hyung-Seok
    Lee, Soo Jin
    Kim, Young Min
    Jang, Hyu Jeong
    Kim, Dong Hwan
    Shin, Jeong-Won
    Kim, Nam-Jung
    RSC ADVANCES, 2021, 11 (23) : 14000 - 14006
  • [3] Palladium (II)-catalyzed Stereoselective Cyclization to the Ether and its Application to the Synthetic Studies of Yessotoxin
    Yokoyama, Hajime
    Miyazawa, Masahiro
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2020, 78 (04) : 317 - 326
  • [4] A NOVEL PENTOSE SYNTHESIS VIA PALLADIUM(II)-CATALYZED CYCLIZATION OF AN UNSTABLE HEMIACETAL
    Awasaguchi, Ken-ichiro
    Miyazawa, Masahiro
    Uoya, Ikuyo
    Inoue, Koichi
    Nakamura, Koji
    Yokoyama, Hajime
    Hirai, Yoshiro
    HETEROCYCLES, 2010, 81 (09) : 2105 - 2121
  • [5] Current state of and need for enzyme engineering of 2-deoxy-D-ribose 5-phosphate aldolases and its impact
    Rouvinen, Juha
    Andberg, Martina
    Paakkonen, Johan
    Hakulinen, Nina
    Koivula, Anu
    APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2021, 105 (16-17) : 6215 - 6228
  • [6] Chiral Coordination Polymers from a New 2-Deoxy-D-ribose Derivative Linker: Syntheses, Structures, and Fe3+ Fluorescent Probe Functions
    He, Tian-Sheng
    Lan, Yan-Long
    Li, Zong-Ying
    Zhu, Li-Na
    Li, Xiao-Zeng
    CRYSTAL GROWTH & DESIGN, 2021, 21 (04) : 2233 - 2242
  • [7] SYNTHETIC STUDIES OF YESSOTOXIN: ITERATIVE SYNTHESIS OF THE AB RING SYSTEM VIA Pd(II)-CATALYZED CYCLIZATION OF ALCOHOL
    Yokoyama, Hajime
    Kusumoto, Yasuhiro
    Sumiyoshi, Koshiro
    Miyazawa, Masahiro
    Hirai, Yoshiro
    HETEROCYCLES, 2014, 89 (02) : 353 - 358
  • [8] Palladium(II)-Catalyzed Asymmetric Tandem Cyclization of 2-Aminoaryl Alkynones: An Approach to Chiral 1,2,3,4-Tetrahydro-β-carbolines
    Chen, Junjie
    Han, Xiuling
    Lu, Xiyan
    ORGANIC LETTERS, 2018, 20 (23) : 7470 - 7473
  • [9] A General Strategy for the Construction of Functionalized Azaindolines via Domino Palladium-Catalyzed Heck Cyclization/Suzuki Coupling
    Schempp, Tabitha T.
    Daniels, Blake E.
    Staben, Steven T.
    Stivala, Craig E.
    ORGANIC LETTERS, 2017, 19 (13) : 3616 - 3619
  • [10] Increasing the Efficiency of the Transannular Diels-Alder Strategy via Palladium(II)-Catalyzed Macrocyclizations
    Iafe, Robert G.
    Kuo, Jonathan L.
    Hochstatter, Dustin G.
    Saga, Tomomi
    Turner, Jonathan W.
    Merlic, Craig A.
    ORGANIC LETTERS, 2013, 15 (03) : 582 - 585