Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids

被引：10

作者：

Marjanovic, Jasna ^{[2
]}

Ferjancic, Zorana ^{[1
]}

Saicic, Radomir N. ^{[1
]}

机构：

[1] Univ Belgrade, Fac Chem, Studentski Trg 16,POB 51, Belgrade 11158, Serbia

[2] Fac Chem, Innovat Ctr, Belgrade, Serbia

来源：

TETRAHEDRON | 2015年 / 71卷 / 38期

关键词：

Organocatalysis; Iminosugars; Fagomine; Pipecolic acids; Glycolipid storage disorders; LYSOSOMAL ALPHA-GALACTOSIDASE; DE-NOVO SYNTHESIS; GLYCOSIDASE INHIBITORS; ASYMMETRIC INDUCTION; FABRY LYMPHOBLASTS; NATURAL OCCURRENCE; ALDOL REACTIONS; DERIVATIVES; 1-DEOXYGALACTONOJIRIMYCIN; MOLECULES;

D O I：

10.1016/j.tet.2015.07.036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective synthesis of 4-epi-fagomine was accomplished starting from dioxanone and Cbz-protected benyzlamine, in 4 steps, with 18% overall yield. The key feature of this synthetic approach is the tactical combination of reactions: organocatalyzed aldolization/reductive amination, which allows for a quick formation of heterocyclic rings with defined absolute configuration of all stereogenic centers. Two hydroxypipecolic acids and a reduced fagomine analogue were also synthesized. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：6784 / 6789

页数：6

共 50 条

[1] Glycal mediated synthesis of piperidine alkaloids: fagomine, 4-epi-fagomine, 2-deoxynojirimycin, and an advanced intermediate, iminoglycal
Chand, Hemender R.
Tiwari, Mritunjay K.
Bhattacharya, Asish K.
RSC ADVANCES, 2022, 12 (51) : 33021 - 33031
[2] Divergent Synthesis of 4-epi-Fagomine, 3,4-Dihydroxypipecolic Acid, and a Dihydroxyindolizidine and Their β-Galactosidase Inhibitory and Immunomodulatory Activities
Kumar, K. S. Ajish
Rathee, J. S.
Subramanian, M.
Chattopadhyay, S.
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (15): : 7406 - 7413
[3] Glycal mediated synthesis of piperidine alkaloids: fagomine, 4-epi-fagomine, 2-deoxynojirimycin, and an advanced intermediate, iminoglycal (vol 12, pg 33021, 2022)
Chand, Hemender R. R.
Tiwari, Mrityunjay K. K.
Bhattacharya, Asish K. K.
RSC ADVANCES, 2022, 12 (53) : 34570 - 34570
[4] Stereoselective synthesis and biological evaluation of D-fagomine, D-3-epi-fagomine and D-3,4-epi-fagomine analogs from D-glyceraldehyde acetonide as a common building block
Alberto Diez, J.
Galvez, Jose A.
Diaz-de-Villegas, Maria D.
Badorrey, Ramon
Bartholomew, Barbara
Nash, Robert J.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (46) : 9278 - 9286
[5] Silicon-mediated asymmetric synthesis of fagomine and 3,4-di-epi-fagomine
Kundu, Pintu K.
Ghosh, Sunil K.
TETRAHEDRON-ASYMMETRY, 2011, 22 (10) : 1090 - 1096
[6] Erratum: Glycal mediated synthesis of piperidine alkaloids: fagomine, 4-epi-fagomine, 2-deoxynojirimycin, and an advanced intermediate, iminoglycal (RSC Advances (2022) 12 (33021-33031) DOI: 10.1039/D2RA05224E)
Chand, Hemender R.
Tiwari, Mrityunjay K.
Bhattacharya, Asish K.
RSC Advances, 2022, 12 (53)
[7] STEREOSELECTIVE SYNTHESIS OF PIPECOLIC ACIDS
ANGLE, SR
ARNAIZ, DO
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 196 : 229 - ORGN
[8] SYNTHESIS AND RESOLUTION OF SUBSTITUTED PIPECOLIC ACIDS
OVERBERGER, CG
SHALATI, MD
EUROPEAN POLYMER JOURNAL, 1983, 19 (10-1) : 1055 - 1065
[9] STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED PIPECOLIC ACIDS
ANGLE, SR
ARNAIZ, DO
TETRAHEDRON LETTERS, 1989, 30 (05) : 515 - 518
[10] An efficient, asymmetric synthesis of pipecolic acid and 2-alkyl pipecolic acids
Hou, DR
Hung, SY
Hu, CC
TETRAHEDRON-ASYMMETRY, 2005, 16 (23) : 3858 - 3864

← 1 2 3 4 5 →