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
  • [1] Novel enantioselective synthesis of penaresidin A and allo-penaresidin A via the construction of a highly functionalized azetidine
    Liu, DG
    Lin, GQ
    TETRAHEDRON LETTERS, 1999, 40 (02) : 337 - 340
  • [2] Concise enantioselective synthesis of diospongins A and B
    Stefan, Eric
    Nalin, Ansel P.
    Taylor, Richard E.
    TETRAHEDRON, 2013, 69 (36) : 7706 - 7712
  • [3] A Simple Enantioselective Route to Functionalized Indolizidines: Synthesis of (+)-Ipalbidine and (+)-Antofine
    Pansare, Sunil V.
    Lingampally, Rajinikanth
    Dyapa, Rajendar
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (12) : 2235 - 2238
  • [4] A practical route to enantiopure, highly functionalized seven-membered carbocycles and tetrahydrofurans:: Concise synthesis of (+)-nemorensic acid
    López, F
    Castedo, L
    Mascareñas, JL
    CHEMISTRY-A EUROPEAN JOURNAL, 2002, 8 (04) : 884 - 899
  • [5] Catalytic Enantioselective Synthesis of Highly Functionalized Difluoromethylated Cyclopropanes
    Bos, Maxence
    Huang, Wei-Sheng
    Poisson, Thomas
    Pannecoucke, Xavier
    Charette, Andre B.
    Jubault, Philippe
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (43) : 13319 - 13323
  • [6] Highly Enantioselective Catalytic Synthesis of Functionalized Chiral Diazoacetoacetates
    Xu, Xinfang
    Hu, Wen-Hao
    Doyle, Michael P.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (28) : 6392 - 6395
  • [7] Organocatalytic Enantioselective Synthesis of Highly Functionalized Polysubstituted Pyrrolidines
    Ruiz, Nerea
    Reyes, Efraim
    Vicario, Jose L.
    Badia, Dolores
    Carrillo, Luisa
    Uria, Uxue
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (30) : 9357 - 9367
  • [8] Stereocontrolled Synthesis of Highly Functionalized Quaternary Carbon Centers: A Route to α-Substituted Serines
    Ariza, Xavier
    Cornella, Josep
    Font-Bardia, Merce
    Garcia, Jordi
    Ortiz, Jordi
    Sanchez, Carolina
    Solans, Xavier
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) : 4202 - 4205
  • [9] Enantioselective Synthesis of Deoxymannojirimycin Based on Sharpless Asymmetric Epoxidation of a Highly Functionalized Allylic Alcohol
    Lamas, Marie-Celine
    Malacria, Max
    Thorimbert, Serge
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (15) : 2777 - 2780
  • [10] A highly stereocontrolled route to 2-(2′-oxiranyl)piperidines and pyrrolidines: enantioselective synthesis of (+)-α-conhydrine
    Rodriguez, Didac
    Pico, Anna
    Moyano, Albert
    TETRAHEDRON LETTERS, 2008, 49 (48) : 6866 - 6869