Total synthesis of (+)-lentiginosine from D-glucose

被引：39

作者：

Alam, Mohammad Abrar ^{[1
]}

Vankar, Yashwant D. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 38期

关键词：

(+)-lentiginosine; D-glucose; epoxide; barton deoxygenation;

D O I：

10.1016/j.tetlet.2008.07.057

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of (+)-lentiginosine, a potent and selective amyloglucosidase inhibitor, is reported from a D-glucose-derived epoxide in 38% overall yield. in this synthesis, ambient conditions and readily able starting materials and reagents are used. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：5534 / 5536

页数：3

共 48 条

[1] ENANTIOSELECTIVE SYNTHESIS OF SWAINSONINE, A TRIHYDROXYLATED INDOLIZIDINE ALKALOID [J].

ADAMS, CE ;

WALKER, FJ ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (03) :420-422

[2] Administration of miglitol until 30 min after the start of a meal is effective in type 2 diabetic patients [J].

Aoki, Kazutaka ;

Nakamura, Akinobu ;

Ito, Satoshi ;

Nezu, Uru ;

Iwasaki, Tomoyuki ;

Takahashi, Mayumi ;

Kimura, Mari ;

Terauchi, Yasuo .

DIABETES RESEARCH AND CLINICAL PRACTICE, 2007, 78 (01) :30-33

[3] Glycosidase inhibitors: update and perspectives on practical use [J].

Asano, N .

GLYCOBIOLOGY, 2003, 13 (10) :93R-104R

[4] Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application [J].

Asano, N ;

Nash, RJ ;

Molyneux, RJ ;

Fleet, GWJ .

TETRAHEDRON-ASYMMETRY, 2000, 11 (08) :1645-1680

[5] ACARBOSE - AN UPDATE OF ITS PHARMACOLOGY AND THERAPEUTIC USE IN DIABETES-MELLITUS [J].

BALFOUR, JA ;

MCTAVISH, D .

DRUGS, 1993, 46 (06) :1025-1054

[6] ASYMMETRIC-SYNTHESIS OF ENANTIOMERICALLY PURE 4'-FLUOROALKYL-2',3'-DIDEOXY NUCLEOSIDES [J].

BRAVO, P ;

MELE, A ;

SALANI, G ;

VIANI, F .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (13) :1577-1580

[7] Inhibition of glycosphingolipid biosynthesis: Application to lysosomal storage disorders [J].

Butters, TD ;

Dwek, RA ;

Platt, FM .

CHEMICAL REVIEWS, 2000, 100 (12) :4683-+

[8] New concise total synthesis of (+)-lentiginosine and some structural analogues [J].

Cardona, F ;

Moreno, G ;

Guarna, F ;

Vogel, P ;

Schuetz, C ;

Merino, P ;

Goti, A .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6552-6555

[9] (+)-lentiginosine, a potent and selective inhibitor of amyloglucosidase: Synthetic efforts and disputes on its absolute configuration [J].

Cardona, Francesca ;

Goti, Andrea ;

Brandi, Alberto .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (10) :1551-1565

[10] Synthesis of (-)-lentiginosine, its 8a-epimer and dihydroxylated pyrrolizidine alkaloid from D-glucose [J].

Chaudhari, VD ;

Kumar, KSA ;

Dhavale, DD .

TETRAHEDRON, 2006, 62 (18) :4349-4354

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