Bicyclo[3.3.0]octanone formation by Fe(III) mediated ring expansion transannular cyclisation reactions of cyclopropyl ethers

被引：8

作者：

Booker-Milburn, KI ^{[1
]}

Dainty, RF ^{[1
]}

机构：

[1] Univ E Anglia, Sch Chem Sci, Norwich NR4 7TJ, Norfolk, England

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 28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(98)00935-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Substituted bicyclo[5.1.0]octene derivatives undergo facile Fe(III) mediated radical ring expansion-transannular cyclisation reactions to give the corresponding bicyclo[3.3.0]octanones. (C) 1998 Elsevier Science Ltd, All rights reserved.

引用

页码：5097 / 5100

页数：4

共 12 条

[1] Diastereoselective Fe(III) mediated oxidative cyclisation reactions of cyclopropanone acetals [J].

Booker-Milburn, KI ;

Barker, A ;

Brailsford, W .

TETRAHEDRON LETTERS, 1998, 39 (24) :4373-4376

[2] Iron(III)-mediated oxidative cyclisations of cyclopropanone acetals [J].

BookerMilburn, KI ;

Cox, B ;

Mansley, TE .

CHEMICAL COMMUNICATIONS, 1996, (22) :2577-2578

[3] IRON(III) MEDIATED TRANSFORMATIONS OF CYCLOPROPYLTRIMETHYLSILYL ETHERS .1. FREE-RADICAL TANDEM RING EXPANSION-CYCLIZATION REACTIONS FOR THE RAPID CONSTRUCTION OF [N30] BICYCLIC RING-SYSTEMS [J].

BOOKERMILBURN, KI ;

THOMPSON, DF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (18) :2315-2321

[4]

BOOKERMILBURN KI, 1992, SYNLETT, P809

[5]

BOOKERMILBURN KI, 1993, SYNLETT, P592

[6] THE TANDEM RADICAL CYCLIZATION APPROACH TO ANGULAR TRIQUINANES - MODEL STUDIES AND THE TOTAL SYNTHESIS OF (+/-)-SILPHIPERFOLENE AND (+/-)-9-EPISILPHIPERFOLENE [J].

CURRAN, DP ;

KUO, SC .

TETRAHEDRON, 1987, 43 (23) :5653-5661

[7] TANDEM RADICAL CYCLIZATION APPROACH TO ANGULAR TRIQUINANES - A SHORT SYNTHESIS OF (+/-)-SILPHIPERFOL-6-ENE AND (+/-)-9-EPISILPHIPERFOL-6-ENE [J].

CURRAN, DP ;

KUO, SC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (05) :1106-1107

[8] DIRECT OXIDATION OF TERTIARY ALLYLIC ALCOHOLS - SIMPLE AND EFFECTIVE METHOD FOR ALKYLATIVE CARBONYL TRANSPOSITION [J].

DAUBEN, WG ;

MICHNO, DM .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (04) :682-685

[9] FREE-RADICAL TRANSANNULAR CYCLOADDITIONS TO CIS-CIS-1,5-CYCLOOCTADIENE [J].

DOWBENKO, R .

TETRAHEDRON, 1964, 20 (08) :1843-&

[10] CONFORMATIONALLY CONSTRAINED ACPD ANALOGS - SYNTHESIS AND RESOLUTION OF 3-AMINOBICYCLO[3,3,0]OCTANE-1,3-DICARBOXYLIC ACIDS [J].

EZQUERRA, J ;

YRURETAGOYENA, B ;

AVENDANO, C ;

DELACUESTA, E ;

GONZALEZ, R ;

PRIETO, L ;

PEDREGAL, C ;

ESPADA, M ;

PROWSE, W .

TETRAHEDRON, 1995, 51 (11) :3271-3278

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