Synthesis of 1,4-diaminocyclitols from L-serine methyl ester

被引：24

作者：

Kang, M ^{[1
]}

Park, J ^{[1
]}

Konradi, AW ^{[1
]}

Pedersen, SF ^{[1
]}

机构：

[1] UNIV CALIF BERKELEY,DEPT CHEM,BERKELEY,CA 94720

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 16期

关键词：

D O I：

10.1021/jo960691a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

L-Serine methyl ester hydrochloride was converted to (S)-2-[N-(benzyloxycarbonyl)amino]-3-(tert-butyldimethylsiloxy)propanal (6). Homocoupling of 6 promoted by [V2Cl3(THF)(6)](2)[Zn2Cl6] (1) gave C-2-symmetric diol (7). After manipulation of protecting groups and Swern oxidation, 7 was converted to a 1,6-dialdehyde 10. Intramolecular pinacol coupling of 10 with 1 gave a selectively protected 1,4-diamino-2,3,5,6-tetrahydroxycyclohexane, which is the key skeleton of Fortimicin AM and AK.

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页码：5528 / 5531

页数：4

相关论文

共 17 条

[1] FORTIMICINS-A AND FORTIMICINS-B, NEW AMINOGLYCOSIDE ANTIBIOTICS .3. STRUCTURAL IDENTIFICATION [J].

EGAN, RS ;

STANASZEK, RS ;

CIROVIC, M ;

MUELLER, SL ;

TADANIER, J ;

MARTIN, JR ;

COLLUM, P ;

GOLDSTEIN, AW ;

DEVAULT, RL ;

SINCLAIR, AC ;

FAGER, EE ;

MITSCHER, LA .

JOURNAL OF ANTIBIOTICS, 1977, 30 (07) :552-563

[2] INTERMOLECULAR PINACOL CROSS COUPLING OF ELECTRONICALLY SIMILAR ALDEHYDES - AN EFFICIENT AND STEREOSELECTIVE SYNTHESIS OF 1,2-DIOLS EMPLOYING A PRACTICAL VANADIUM(II) REAGENT [J].

FREUDENBERGER, JH ;

KONRADI, AW ;

PEDERSEN, SF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) :8014-8016

[3] SYNTHESIS OF (-)-FORTAMINE AND (+)-2-DEOXYFORTAMINE FROM RESOLVED 3S4S-N-CARBOMETHOXY-3-AMINOCYCLOHEXENE-4-O1 [J].

KNAPP, S ;

SEBASTIAN, MJ ;

RAMANATHAN, H ;

BHARADWAJ, P ;

POTENZA, JA .

TETRAHEDRON, 1986, 42 (13) :3405-3410

[4] TOTAL SYNTHESIS OF (+/-)-FORTAMINE AND (+/-)-2-DEOXYFORTAMINE [J].

KNAPP, S ;

SEBASTIAN, MJ ;

RAMANATHAN, H .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (24) :4786-4788

[5] THE 1ST ENANTIOSELECTIVE SYNTHESIS OF FORTAMINE, THE 1,4-DIAMINOCYCLITOL MOIETY OF FORTIMICIN-A, BY CHEMICOENZYMATIC APPROACH [J].

KOBAYASHI, S ;

KAMIYAMA, K ;

OHNO, M .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04) :1169-1177

[6] PINACOL HOMOCOUPLING OF (S)-2-[N-(BENZYLOXYCARBONYL)AMINO] ALDEHYDES BY [V2CL3(THF)6]2[ZN2CL6] - SYNTHESIS OF C2-SYMMETRICAL (1S,2R,3R,4S)-1,4-DIAMINO 2,3-DIOLS [J].

KONRADI, AW ;

PEDERSEN, SF .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (01) :28-32

[7] PINACOL CROSS-COUPLING OF 2-[N-(ALKOXYCARBONYL)AMINO] ALDEHYDES AND ALIPHATIC-ALDEHYDES BY [V2CL3(THF)(6)](2)[ZN2CL6] - SYNTHESIS OF SYN,SYN-3-[N-(ALKOXYCARBONYL)AMINO] 1,2-DIOLS [J].

KONRADI, AW ;

KEMP, SJ ;

PEDERSEN, SF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (04) :1316-1323

[8] STEREOSELECTIVE SYNTHESIS OF 3-AMINO 1,2-DIOLS VIA INTERMOLECULAR PINACOL CROSS-COUPLING OF ALPHA-[(ALKOXYCARBONYL)AMINO] ALDEHYDES WITH ALIPHATIC-ALDEHYDES - SHORT ASYMMETRIC SYNTHESES OF 2 2,3,6-TRIDEOXY-3-AMINO SUGARS [J].

KONRADI, AW ;

PEDERSEN, SF .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4506-4508

[9]

KUO CH, 1984, TETRAHEDRON LETT, V25, P3429

[10] ENANTIOSELECTIVE SYNTHESIS OF (+)-FORTAMINE [J].

LIU, PL ;

VANDEWALLE, M .

TETRAHEDRON LETTERS, 1993, 34 (22) :3625-3628