Intramolecular Michael addition of benzylamine to sugar derived α,β-unsaturated ester:: a new diastereoselective synthesis of a higher homologue of 1-deoxy-L-ido-nojirimycin

被引：35

作者：

Desai, VN ^{[1
]}

Saha, NN ^{[1
]}

Dhavale, DD ^{[1
]}

机构：

[1] Univ Poona, Dept Chem, Garware Res Ctr, Poona 411007, Maharashtra, India

来源：

CHEMICAL COMMUNICATIONS | 1999年 / 17期

关键词：

D O I：

10.1039/a905440e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The diastereoselective intramolecular Michael addition of the benzylamine generated in situ from hemiacetal 3 leads to the lactone 4a with the required homoazasugar ring skeleton; reduction of the lactone functionality and removal of the protecting groups afford 1-deoxy-L-ido-homonojirimycin.

引用

页码：1719 / 1720

页数：2

共 27 条

[1] Michael addition of N- and O-centred nucleophiles to tethered acrylates. The role of double bond geometry in controlling the diastereoselectivity of cyclisations leading to 2,6-disubstituted tetrahydropyrans and piperidines [J].

Banwell, MG ;

Bui, CT ;

Pham, HTT ;

Simpson, GW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (10) :967-969

[2] TANDEM SN2-MICHAEL REACTIONS FOR THE PREPARATION OF SIMPLE 5-MEMBERED AND 6-MEMBERED-RING NITROGEN AND SULFUR HETEROCYCLES [J].

BUNCE, RA ;

PEEPLES, CJ ;

JONES, PB .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1727-1733

[3] The synthesis of ester and ketone analogues of 1-deoxynojirimycin and castanospermine [J].

Compernolle, F ;

Joly, G ;

Peeters, K ;

Toppet, S ;

Hoornaert, G ;

Kilonda, A ;

BabadyBila .

TETRAHEDRON, 1997, 53 (37) :12739-12754

[4] Synthesis of 1,6-dideoxynojirimycin, 1,6-dideoxy-D-allo-nojirimycin, and 1,6-dideoxy-D-gulo-nojirimycin via asymmetric hetero-Diels-Alder reactions [J].

Defoin, A ;

Sarazin, H ;

Streith, J .

HELVETICA CHIMICA ACTA, 1996, 79 (02) :560-567

[5] 6-deoxy-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and D-series, D-fuco-nojirimycin and their 1-deoxyderivatives via hetero-Diels-Alder cycloadditions. [J].

Defoin, A ;

Sarazin, H ;

Streith, J .

TETRAHEDRON, 1997, 53 (40) :13783-13796

[6] 6-deoxy-allo-nojirimycin in the racemic and D-series, 6-deoxy-D,L-talo-nojirimycin, their 1-deoxyderivatives and 6-deoxy-2-D,L-allosamine via hetero-Diels-Alder cycloadditions. [J].

Defoin, A ;

Sarazin, H ;

Streith, J .

TETRAHEDRON, 1997, 53 (40) :13769-13782

[7] A new route to aminosugars from sugar nitrones: synthesis of 6-deoxynojirimycin [J].

Dhavale, DD ;

Desai, VN ;

Sindkhedkar, MD ;

Mali, RS ;

Castellari, C ;

Trombini, C .

TETRAHEDRON-ASYMMETRY, 1997, 8 (09) :1475-1486

[8]

ELIEL EL, 1994, STEREOCHEMISTRY ALKE, P579

[9] Synthesis of chiral nonracemic homo-1-deoxyazasugars with D-talo-and L-allo-configuration via tandem Wittig [2+3] cycloaddition reaction [J].

Herdeis, C ;

Schiffer, T .

TETRAHEDRON, 1996, 52 (47) :14745-14756

[10] CARBAMATE-MEDIATED FUNCTIONALIZATION OF UNSATURATED ALCOHOLS .3. INTRAMOLECULAR MICHAEL ADDITION OF O-CARBAMATES TO ALPHA,BETA-UNSATURATED ESTERS - A NEW DIASTEREOSELECTIVE AMINATION IN AN ACYCLIC SYSTEM [J].

HIRAMA, M ;

SHIGEMOTO, T ;

YAMAZAKI, Y ;

ITO, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (06) :1797-1798

← 1 2 3 →