Total synthesis of hyacinthacine A1, a glycosidase inhibitor

被引：46

作者：

Chandrasekhar, Srivari ^{[1
]}

Parida, Bibhuti Bhusan ^{[1
]}

Rambabu, Chegondi ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 19期

关键词：

D O I：

10.1021/jo801377s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical and enantioselective total synthesis of hyacinthacine A(1), is achieved involving syn allylic epoxide opening with retention using Pd catalysis and "domino" hydrogenation (five steps in one pot) sequences.

引用

页码：7826 / 7828

页数：3

共 46 条

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

Asano, N .

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

[2] 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

[3] New polyhydroxylated pyrrolizidine alkaloids from Muscari armeniacum:: structural determination and biological activity [J].

Asano, N ;

Kuroi, H ;

Ikeda, K ;

Kizu, H ;

Kameda, Y ;

Kato, A ;

Adachi, I ;

Watson, AA ;

Nash, RJ ;

Fleet, GWJ .

TETRAHEDRON-ASYMMETRY, 2000, 11 (01) :1-8

[4] Asymmetric routes to substituted piperidines [J].

Bailey, PD ;

Millwood, PA ;

Smith, PD .

CHEMICAL COMMUNICATIONS, 1998, (06) :633-640

[5] SYNTHETIC APPROACHES TO STEREOISOMERS AND ANALOGS OF CASTANOSPERMINE [J].

BURGESS, K ;

HENDERSON, I .

TETRAHEDRON, 1992, 48 (20) :4045-4066

[6] Total syntheses of hyacinthacine A2 and 7-deoxycasuarine by cycloaddition to a carbohydrate derived nitrone [J].

Cardona, F ;

Faggi, E ;

Liguori, F ;

Cacciarini, M ;

Goti, A .

TETRAHEDRON LETTERS, 2003, 44 (11) :2315-2318

[7] Recent advances in the stereoselective synthesis of hydroxylated pyrrolizidines - A review [J].

Casiraghi, G ;

Zanardi, F ;

Rassu, G ;

Pinna, L .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1996, 28 (06) :641-+

[8] Total synthesis of (-)-lentiginosine [J].

Chandrasekhar, S. ;

Vijaykumar, B. V. D. ;

Pratap, T. V. .

TETRAHEDRON-ASYMMETRY, 2008, 19 (06) :746-750

[9] Asymmetric synthesis of (+)-tetrahydropseudodistomin [J].

Chandrasekhar, S. ;

Sultana, S. Shameem ;

Kiranmai, N. ;

Narsihmulu, Ch. .

TETRAHEDRON LETTERS, 2007, 48 (13) :2373-2375

[10] Practical and highly stereoselective approaches to the total synthesis of (-)-codonopsinine [J].

Chandrasekhar, Srivari ;

Saritha, Birudaraju ;

Jagadeshwar, Vannada ;

Prakash, Samala Jaya .

TETRAHEDRON-ASYMMETRY, 2006, 17 (09) :1380-1386

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