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

[41] Difluoromethylenated polyhydroxylated pyrrolidines: facile synthesis, crystal structure and biological evaluation
Wang, Ruo-Wen
Xu, Jun
Lopez, Oscar
Bols, Mikael
Qing, Feng-Ling
FUTURE MEDICINAL CHEMISTRY, 2009, 1 (05) : 991 - 997
[42] Hg(II) reagent-controlled stereoselective synthesis of 2,5-cis- and 2,5-trans-polyhydroxylated pyrrolidines
Chikkanna, D
Han, HS
SYNLETT, 2004, (13) : 2311 - 2314
[43] A short and efficient stereoselective synthesis of the polyhydroxylated macrolactone (+)-aspicilin
Dixon, DJ
Foster, AC
Ley, SV
ORGANIC LETTERS, 2000, 2 (02) : 123 - 125
[44] Polyhydroxylated pyrrolidines:: Synthesis of trideoxy-2,5-iminohexitols -: Part VI
Izquierdo, Isidoro
Plaza, Maria T.
Tamayo, Juan A.
Lo Re, Daniele
Sanchez-Cantalejo, Fernando
SYNTHESIS-STUTTGART, 2008, (09): : 1373 - 1378
[45] Synthesis from lactose of new enantiomerically pure polyhydroxylated pyrrolidines with branched structures
Bennis, K
Gelas, J
Thomassigny, C
CARBOHYDRATE RESEARCH, 1995, 279 : 307 - 314
[46] Double diastereocontrol in the synthesis of enantiomerically pure polyoxamic acid
Harwood, LM
Robertson, SM
CHEMICAL COMMUNICATIONS, 1998, (23) : 2641 - 2642
[47] Stereoselective synthesis of pyrrolidines from β′-amino-allylsilanes
Mohr, Peter
Imhoff, Marie-Paule
Reggiani, Flore
TETRAHEDRON LETTERS, 2015, 56 (17) : 2262 - 2264
[48] A fast, efficient and stereoselective synthesis of hydroxy-pyrrolidines
Dangerfield, Emma M.
Gulab, Shivali A.
Plunkett, Catherine H.
Timmer, Mattie S. M.
Stocker, Bridget L.
CARBOHYDRATE RESEARCH, 2010, 345 (10) : 1360 - 1365
[49] A stereoselective and short total synthesis of the polyhydroxylated γ-amino acid (-)-detoxinine, based on stereoselective preparation of dihydropyrrole derivatives from lithiated alkoxyallenes
Flögel, O
Amombo, MGO
Reissig, HU
Zahn, G
Brüdgam, I
Hartl, H
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (06) : 1405 - 1415
[50] Acid-catalyzed cyclization of vinylsilanes bearing an amino group. Stereoselective synthesis of pyrrolidines
Miura, K
Hondo, T
Nakagawa, T
Takahashi, T
Hosomi, A
ORGANIC LETTERS, 2000, 2 (03) : 385 - 388

← 1 2 3 4 5 →