Asymmetric synthesis of 2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazoles

被引：26

作者：

Cliff, MD ^{[1
]}

Pyne, SG ^{[1
]}

机构：

[1] UNIV WOLLONGONG,DEPT CHEM,WOLLONGONG,NSW 2522,AUSTRALIA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 04期

关键词：

D O I：

10.1021/jo961630f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for preparing the eight stereoisomers of the biologically active compound (1R,2S,3R)-2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole (THI, 1) is reported. This method employs a palladium(0)-catalyzed coupling of 1-(ethoxymethyl)-4-iodoimidazole (7) to functionalized vinylstannanes (R)- or (S)-12a,b or 13a,b or 1-alkynylstannanes (R)- or (S)-6a,b to introduce the C-4 imidazole four-carbon side chain. The 1,2-dihydroxy functionality of the butyl side chain was introduced by Sharpless catalytic asymmetric dihydroxylation reactions.

引用

页码：1023 / 1032

页数：10

共 33 条

[1] Enantioselective total synthesis of (+)-duocarmycin A, epi-(+)-duocarmycin A, and their unnatural enantiomers [J].

Boger, DL ;

McKie, JA ;

Nishi, T ;

Ogiku, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (09) :2301-2302

[2] SYNTHESIS OF (+)-ZARAGOZIC ACID-C [J].

CARREIRA, EM ;

DUBOIS, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (23) :10825-10826

[3] ON STEREOCHEMISTRY OF OSMIUM TETRAOXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE [J].

CHA, JK ;

CHRIST, WJ ;

KISHI, Y .

TETRAHEDRON, 1984, 40 (12) :2247-2255

[4]

Cliff Matthew D., 1995, Tetrahedron Letters, V36, P5969, DOI 10.1016/0040-4039(95)01155-B

[5] DIRECT SYNTHESIS OF TRIMETHYLVINYLSTANNANES FROM ALDEHYDES [J].

CLIFF, MD ;

PYNE, SG .

TETRAHEDRON LETTERS, 1995, 36 (05) :763-766

[6] ASYMMETRIC-SYNTHESIS OF 2-ACETYL-4(5)-(1,2,4-TRIHYDROXYBUTYL)IMIDAZOLES [J].

CLIFF, MD ;

PYNE, SG .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (08) :2378-2383

[7]

Corey E.J., 1972, TETRAHEDRON LETT, V13, P3769, DOI DOI 10.1016/S0040-4039(01)94157-7

[8] IMPROVED ENANTIOSELECTIVITY IN ASYMMETRIC DIHYDROXYLATIONS OF TERMINAL OLEFINS USING PYRIMIDINE LIGANDS [J].

CRISPINO, GA ;

JEONG, KS ;

KOLB, HC ;

WANG, ZM ;

XU, DQ ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3785-3786

[9] LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS [J].

FARINA, V ;

KRISHNAN, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9585-9595

[10]

GOLIN SJP, 1991, CLIN EXP IMMUNOL, V85, P335

← 1 2 3 4 →