New method for the synthesis of α-substituted tetrahydrofuran-2-methanols through diastereoselective addition of THF to aldehydes mediated by Et3B in the presence of air

被引：45

作者：

Yoshimitsu, T ^{[1
]}

Tsunoda, M ^{[1
]}

Nagaoka, H ^{[1
]}

机构：

[1] Meiji Pharmaceut Univ, Tokyo 2048588, Japan

来源：

CHEMICAL COMMUNICATIONS | 1999年 / 17期

关键词：

D O I：

10.1039/a904745j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The tetrahydrofuranyl radical, generated from THF with Et3B in the presence of air, was found to react with aldehydes threo-selectively to afford alpha-substituted tetrahydrofuran-2-methanols, the common structural motifs of biologically active acetogenin polyketides, in moderate yields.

引用

收藏

页码：1745 / 1746

页数：2

相关论文

共 32 条

[1] Annonaceous acetogenins: Recent progress [J].

Alali, FQ ;

Liu, XX ;

McLaughlin, JL .

JOURNAL OF NATURAL PRODUCTS, 1999, 62 (03) :504-540

[2] ORGANIC SYNTHESES VIA FREE-RADICAL DISPLACEMENT REACTIONS OF ORGANOBORANES [J].

BROWN, HC ;

MIDLAND, MM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1972, 11 (08) :692-&

[3]

Cave A, 1997, Fortschr Chem Org Naturst, V70, P81

[4]

Champdore M, 1998, TETRAHEDRON LETT, V39, P9781

[5] Synthesis of styryl tetrahydrofurans and tetrahydropyrans via addition of radicals to unsaturated sulfimides. [J].

Clark, AJ ;

Rooke, S ;

Sparey, TJ ;

Taylor, PC .

TETRAHEDRON LETTERS, 1996, 37 (06) :909-912

[6] 2-FLASK PREPARATION OF ALPHA-LITHIO CYCLIC ETHERS FROM GAMMA-LACTONES AND DELTA-LACTONES - REDUCTIVE LITHIATION AS A ROUTE, VIA RADICAL INTERMEDIATES, TO AXIAL 2-LITHIOTETRAHYDROPYRANS AND THEIR EQUILIBRATION TO THE EQUATORIAL ISOMERS [J].

COHEN, T ;

LIN, MT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (04) :1130-1131

[7] SYNTHESES OF ACETOGENINS OF ANNONACEAE - A NEW CLASS OF BIOACTIVE POLYKETIDES [J].

FIGADERE, B .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (09) :359-365

[8]

Figadere B., 1996, Stud. Nat. Prod. Chem, V18, P193

[9] STEREOCHEMISTRY OF MONO-TETRAHYDROFURANYL MOIETY IN CYTOTOXIC POLYKETIDES .A. SYNTHESIS OF MODEL COMPOUNDS [J].

GALE, JB ;

YU, JG ;

HU, XFE ;

KHARE, A ;

HO, DK ;

CASSADY, JM .

TETRAHEDRON LETTERS, 1993, 34 (37) :5847-5850

[10] Stereocontrolled total synthesis of an annonacin A-type acetogenin: Pseudoannonacin A? [J].

Hanessian, S ;

Grillo, TA .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :1049-1057

← 1 2 3 4 →