Total syntheses of hyacinthacine A2 and 7-deoxycasuarine by cycloaddition to a carbohydrate derived nitrone

被引：146

作者：

Cardona, F ^{[1
]}

Faggi, E ^{[1
]}

Liguori, F ^{[1
]}

Cacciarini, M ^{[1
]}

Goti, A ^{[1
]}

机构：

[1] Univ Florence, Dipartimento Chim Organ Ugo Schiff, I-50019 Sesto Fiorentino, Firenze, Italy

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 11期

关键词：

glycosidases inhibitors; pyrrolizidine alkaloids; nitrones; carbohydrates; enantiospecific synthesis;

D O I：

10.1016/S0040-4039(03)00239-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Practical syntheses of nitrone 8 by two different approaches from sugars are reported. Its use as a versatile intermediate in highly selective 1,3-dipolar cycloaddition reactions constitutes the key step for novel total syntheses of hyacinthacine A(2) (3) and 7-deoxycasuarine (20) by simple transformations of a common isoxazolidine adduct. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：2315 / 2318

页数：4

共 44 条

[1] Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application
Asano, N
Nash, RJ
Molyneux, RJ
Fleet, GWJ
[J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (08) : 1645 - 1680
[2] New polyhydroxylated pyrrolizidine alkaloids from Muscari armeniacum:: structural determination and biological activity
Asano, N
Kuroi, H
Ikeda, K
Kizu, H
Kameda, Y
Kato, A
Adachi, I
Watson, AA
Nash, RJ
Fleet, GWJ
[J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (01) : 1 - 8
[3] Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis
Asano, N
Kato, A
Miyauchi, M
Kizu, H
Kameda, Y
Watson, AA
Nash, RJ
Fleet, GWJ
[J]. JOURNAL OF NATURAL PRODUCTS, 1998, 61 (05): : 625 - 628
[4] Behr JB, 2002, EUR J ORG CHEM, V2002, P1256, DOI 10.1002/1099-0690(200204)2002:7<1256::AID-EJOC1256>3.0.CO
[5] 2-R
[6] Synthesis of casuarines [pentahydroxylated pyrrolizidines] by sodium hydrogen telluride-induced cyclisations of azidodimesylates
Bell, AA
Pickering, L
Watson, AA
Nash, RJ
Pan, YT
Elbein, AD
Fleet, GWJ
[J]. TETRAHEDRON LETTERS, 1997, 38 (33) : 5869 - 5872
[7] Straightforward synthesis of enantiomerically pure (3S,4R)- and (3R,4S)-3,4-isopropylidenedioxypyrroline 1-oxide, precursors of functionalized cis-dihydroxy azaheterocycles, by a novel "one-pot" procedure
Cicchi, S
Corsi, M
Brandi, A
Goti, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (05) : 1678 - 1681
[8] Synthesis of (-)-7-epiaustraline and (-)-1-epicastanospermine
Denmark, SE
Herbert, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) : 2887 - 2896
[9] Synthesis of (+)-casuarine
Denmark, SE
Hurd, AR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) : 2875 - 2886
[10] Synthesis of (1R,2R,3R,7R,7aR)-hexahydro-3-(hydroxymethyl)-1H-pyrrolizine-1,2,7-triol-7-epiaustraline
Denmark, SE
Herbert, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (29) : 7357 - 7358

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