Asymmetric synthesis of the four possible fagomine isomers

被引：80

作者：

Takahata, H ^{[1
]}

Banba, Y

Ouchi, H

Nemoto, H

Kato, A

Adachi, I

机构：

[1] Tohoku Pharmaceut Univ, Fac Pharmaceut Sci, Sendai, Miyagi 9818558, Japan

[2] Toyama Med & Pharmaceut Univ, Fac Pharmaceut Sci, Toyama 9300194, Japan

[3] Toyama Med & Pharmaceut Univ, Dept Hosp Pharm, Toyama 9300194, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 09期

关键词：

D O I：

10.1021/jo034137u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric synthesis of fagomine and its congeners 1-4 has been achieved by catalytic ring-closing metathesis (RCM). The synthesis involved the construction of the piperidene-type chiral building block 5 followed by dihydroxylation, starting from the D-serine-derived Garner aldehyde 6.

引用

页码：3603 / 3607

页数：5

共 28 条

[1] In vitro inhibition and intracellular enhancement of lysosomal α-galactosidase A activity in Fabry lymphoblasts by 1-deoxygalactonojirimycin and its derivatives [J].

Asano, N ;

Ishii, S ;

Kizu, H ;

Ikeda, K ;

Yasuda, K ;

Kato, A ;

Martin, OR ;

Fan, JQ .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 2000, 267 (13) :4179-4186

[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] Asymmetric synthesis of fagomine and its congeners [J].

Banba, Y ;

Abe, C ;

Nemoto, H ;

Kato, A ;

Adachi, I ;

Takahata, H .

TETRAHEDRON-ASYMMETRY, 2001, 12 (06) :817-819

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

Butters, TD ;

Dwek, RA ;

Platt, FM .

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

[5]

Campbell AD, 1998, SYNTHESIS-STUTTGART, P1707

[6] CATALYTIC EPOXIDATION OF ALKENES WITH OXONE [J].

DENMARK, SE ;

FORBES, DC ;

HAYS, DS ;

DEPUE, JS ;

WILDE, RG .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1391-1407

[7]

Dondoni A., 1999, ORG SYNTH, V77, P64

[8] Development of the directed dihydroxylation reaction [J].

Donohoe, TJ .

SYNLETT, 2002, (08) :1223-1232

[9] Homoallylic alcohols and trichloroacetamides as hydrogen bond donors for directed dihydroxylation [J].

Donohoe, TJ ;

Mitchell, L ;

Waring, MJ ;

Helliwell, M ;

Bell, A ;

Newcombe, NJ .

TETRAHEDRON LETTERS, 2001, 42 (51) :8951-8954

[10]

EFFENBERGER F, 1992, LIEBIGS ANN CHEM, P1211

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