A concise route to the highly-functionalized azetidine precursor: the enantioselective synthesis of penaresidin B

被引:14
|
作者
Ding, Feiqing [1 ]
William, Ronny [1 ]
Kock, Si Min [1 ]
Leow, Min Li [1 ]
Liu, Xue-Wei [1 ]
机构
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
关键词
STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; ALKALOIDS; MITSUNOBU;
D O I
10.1039/c4cc09904d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient and high-yielding synthesis of penaresidin B is disclosed herein. The concise 8-step synthesis of azetidine aldehyde was devised by incorporating our novel strategy for ready access to 3-amino-2,3-dideoxysugars via regio- and stereoselective tandem hydroamination/glycosylation of glycal as the key step.
引用
收藏
页码:4639 / 4642
页数:4
相关论文
共 39 条
  • [21] A Highly Enantioselective Synthesis of Functionalized 2,3-Dihydrofurans by a Modified Feist-Benary Reaction
    Dou, Xiaowei
    Zhong, Fangrui
    Lu, Yixin
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (44) : 13945 - 13948
  • [22] CAL-B catalyzed enantioselective synthesis of cyanohydrins - A facile route to versatile building blocks
    Hanefeld, U
    Li, YX
    Sheldon, RA
    Maschmeyer, T
    SYNLETT, 2000, (12) : 1775 - 1776
  • [23] An Organocatalytic Domino Thia-Michael/Aldol Condensation Reaction: Highly Enantioselective Synthesis of Functionalized Dihydrothiophenes
    Tang, Jie
    Xu, Dan Qian
    Xia, Ai Bao
    Wang, Yi Feng
    Jiang, Jun Rong
    Luo, Shu Ping
    Xu, Zhen Yuan
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (13) : 2121 - 2126
  • [24] Enantioselective Synthesis of Cyclic Thioureas via Mannich Reaction and Concise Synthesis of Highly Optically Active Methylthioimidazolines: Discovery of a More Potent Antipyretic Agent
    Jiang, Xianxing
    Wang, Yiqing
    Zhang, Gen
    Fu, Dan
    Zhang, Futing
    Kai, Ming
    Wang, Rui
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (10) : 1787 - 1796
  • [25] Highly enantioselective aldol reaction of acetaldehyde and isatins only with 4-hydroxydiarylprolinol as catalyst: concise stereoselective synthesis of (R)-convolutamydines B and E, (-)-donaxaridine and (R)-chimonamidine
    Chen, Wen-Bing
    Du, Xi-Lin
    Cun, Lin-Feng
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    TETRAHEDRON, 2010, 66 (07) : 1441 - 1446
  • [26] A Concise and Highly Enantioselective Total Synthesis of(+)-anti- and (-)-syn-Mefloquine Hydrochloride: Definitive Absolute Stereochemical Assignment of the Mefloquines
    Rastelli, Ettore J.
    Coltart, Don M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) : 14070 - 14074
  • [27] Highly Enantioselective Epoxidation Catalyzed by Cinchona Thioureas: Synthesis of Functionalized Terminal Epoxides Bearing a Quaternary Stereogenic Center
    Russo, Alessio
    Galdi, Gerardina
    Croce, Gianluca
    Lattanzi, Alessandra
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (20) : 6152 - 6157
  • [28] Dearomative Indole [5+2] Cycloaddition Reactions: Stereoselective Synthesis of Highly Functionalized Cyclohepta[b]indoles
    Mei, Guangjian
    Yuan, Hao
    Gu, Yueqing
    Chen, Wei
    Chung, Lung Wa
    Li, Chuang-chuang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (41) : 11051 - 11055
  • [29] Diastereocontrolled synthesis of highly functionalized spiroketals:: Application to the synthesis of a precursor of the C-12-C-25 fragment of bafilomycin A1
    Lopez, R
    Poupon, JC
    Prunet, J
    Férézou, JP
    Ricard, L
    SYNTHESIS-STUTTGART, 2005, (04): : 644 - 661
  • [30] Enantioselective synthesis of highly functionalized octahydro-6-oxo-1-phenylnaphthalene-2-carbaldehydes via organocatalytic domino reactions
    Hong, Bor-Cherng
    Nimje, Roshan Y.
    Liao, Ju-Hsiou
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (15) : 3095 - 3101