Stereoselective strategy for the synthesis of (+)-polyoxamic acid and some polyhydroxylated pyrrolidines

被引：6

作者：

Lingamurthy, Macha ^{[1
]}

Rajender, Anugula ^{[1
]}

Rao, Batchu Venkateswara ^{[1
]}

机构：

[1] Indian Inst Chem Technol, CSIR, Organ & Biomol Chem Div, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 46期

关键词：

Polyoxamic acid; Iminosugars; Glycosidase inhibitors; Stereoselective; Grignard reaction; POLYOXAMIC ACID; CONVENIENT SYNTHESIS; GLYCOSIDASE INHIBITORS; ASYMMETRIC-SYNTHESIS; ANTIMITE SUBSTANCE; NATURAL OCCURRENCE; SPHINGOFUNGIN-C; AMINO-ACIDS; DERIVATIVES; EFFICIENT;

D O I：

10.1016/j.tetlet.2013.08.126

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient strategy for the synthesis of dihydroxy chiral amino moiety which can be utilized for the synthesis of polyoxamic acid, 1,4-dideoxy-1,4-imino-D-xylitol, and dihydroxy pyrrolidine by using highly diastereoselective nucleophilic addition on chiral imine has been reported. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：6189 / 6191

页数：3

共 50 条

[21] Stereoselective synthesis of fluorinated pyrrolidines
Combettes, Lorraine E.
Lozano, Oscar
Schuler, Marie
Patel, Rakesh
Gouverneur, Veronique
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
[22] SYNTHESIS OF POLYHYDROXYLATED PYRROLIDINES, PIPERIDINES, AND OCTAHYDROINDOLIZINES AS GLYCOSIDASE INHIBITORS
FLEET, GWJ
SWAINSONINE AND RELATED GLYCOSIDASE INHIBITORS, 1989, : 382 - 395
[23] Synthesis of amphiphilic polyhydroxylated pyrrolidines as potential glycosidase inhibitors
Esposito, A
Falorni, M
Taddei, M
TETRAHEDRON LETTERS, 1998, 39 (36) : 6543 - 6546
[24] A Rapid Synthesis of 2-Aryl Polyhydroxylated Pyrrolidines
Su, Jia-Kun
Jia, Yue-Mei
He, Ruirui
Rui, Pei-Xin
Han, Nanyin
He, Xihui
Xiang, Junfeng
Chen, Xin
Zhu, Jinghua
Yu, Chu-Yi
SYNLETT, 2010, (11) : 1609 - 1616
[25] A highly efficient and stereoselective synthesis of polyhydroxylated pyrrolidines via regioselective asymmetric aminohydroxylation (RAA) and intramolecular amidomercuration reactions
Singh, S
Chikkanna, D
Singh, OV
Han, HS
SYNLETT, 2003, (09) : 1279 - 1282
[26] Stereoselective Synthesis of Polyhydroxylated Amines Using (S)-Pyroglutamic Acid Derivatives
Ikota, Nobuo
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 2014, 134 (01): : 77 - 88
[27] Asymmetric routes towards polyfunctionalized pyrrolidines: A short diastereoselective synthesis of polyhydroxylated pyrrolidines and an indolizidine
Dudot, B
Micouin, L
Baussanne, I
Royer, J
SYNTHESIS-STUTTGART, 1999, (04): : 688 - 694
[28] A Concise Synthesis of (+)-Polyoxamic Acid and (+)-5-O-Carbamoyl Polyoxamic Acid
Kim, In Su
Li, Qing Ri
Dong, Guang Ri
Woo, Seol Hee
Park, Hyun-ju
Zee, Ok Pyo
Jung, Young Hoon
SYNLETT, 2008, (19) : 2985 - 2988
[29] STEREOSELECTIVE SYNTHESIS OF PYRROLIDINES BY INTRAMOLECULAR HALOAMIDATION
TAMARU, Y
KAWAMURA, S
TANAKA, K
YOSHIDA, Z
HETEROCYCLES, 1985, 23 (01) : 192 - 192
[30] Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines
Hui, Chunngai
Brieger, Lukas
Strohmann, Carsten
Antonchick, Andrey P.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (45) : 18864 - 18870

← 1 2 3 4 5 →