Hydrogen bonding control in the oxidative cyclisation of 1,5-dienes

被引：45

作者：

Donohoe, TJ

Winter, JJG

Helliwell, M

Stemp, G

机构：

[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

[2] SmithKline Beecham Pharmaceut, Harlow CM19 5AW, Essex, England

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 06期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(00)02225-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regioselective dihydroxylation of a series of functionalised polyenes is described. Under acidic conditions, the osmate ester derivatives obtained from oxidation with OsO4/TMEDA undergo an intramolecular cyclisation reaction forming functionalised tetrahydrofurans with high stereoselectivity and in good yield. The generality of this method is illustrated with an application to the synthesis of a bis-tetrahydrofuran ring system. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：971 / 974

页数：4

相关论文

共 14 条

[1] STEREOSPECIFICITY OF OXIDATIVE CYCLO-ADDITION REACTIONS OF 1,5-DIENES [J].

BALDWIN, JE ;

CROSSLEY, MJ ;

LEHTONEN, EMM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (20) :918-920

[2] A syn selective dihydroxylation of cyclic allylic trichloroacetamides using catalytic osmium tetroxide [J].

Blades, K ;

Donohoe, TJ ;

Winter, JJG ;

Stemp, G .

TETRAHEDRON LETTERS, 2000, 41 (24) :4701-4704

[3] Diastereoselective synthesis of tetrahydrofuran-containing fragments by the permanganate oxidation of 1,5,9-trienes [J].

Brown, RCD ;

Hughes, RM ;

Keily, J ;

Kenney, A .

CHEMICAL COMMUNICATIONS, 2000, (18) :1735-1736

[4] Directed dihydroxylation of allylic trichloroacetamides [J].

Donohoe, TJ ;

Blades, K ;

Helliwell, M ;

Moore, PR ;

Winter, JJG ;

Stemp, G .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :2980-2981

[5] The directed dihydroxylation of allylic alcohols [J].

Donohoe, TJ ;

Moore, PR ;

Waring, MJ ;

Newcombe, NJ .

TETRAHEDRON LETTERS, 1997, 38 (28) :5027-5030

[6] syn stereocontrol in the directed dihydroxylation of acyclic allylic alcohols [J].

Donohoe, TJ ;

Newcombe, NJ ;

Waring, MJ .

TETRAHEDRON LETTERS, 1999, 40 (38) :6881-6885

[7] DIE PERMANGANATOXYDATION VON 1,5-DIENVERBINDUNGEN [J].

KLEIN, E ;

ROJAHN, W .

TETRAHEDRON, 1965, 21 (09) :2353-&

[8] Synthesis of salinomycin [J].

Kocienski, PJ ;

Brown, RCD ;

Pommier, A ;

Procter, M ;

Schmidt, B .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (01) :9-39

[9] RuO4-catalysed oxidative cyclisation of 1,6-dienes to trans-2,6-bis(hydroxymethyl)tetrahydropyranyldiols.: A novel stereoselective process [J].

Piccialli, V .

TETRAHEDRON LETTERS, 2000, 41 (19) :3731-3733

[10] A STEREOSELECTIVE SYNTHESIS OF THE TETRAHYDROFURAN UNIT IN IONOMYCIN [J].

SPINO, C ;

WEILER, L .

TETRAHEDRON LETTERS, 1987, 28 (07) :731-734