Fe(III)/Cu(II) mediated 5- and 6-exo oxidative ring expansion/cyclisation of cyclopropyl ethers:: studies towards dictyol C and α-eudesmol

被引：11

作者：

Booker-Milburn, KI

Cox, B

Grady, M

Halley, F

Marrison, S

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

[2] Glaxo Wellcome Res & Dev Ltd, Med Res Ctr, Stevenage SG1 2NY, Herts, England

[3] Aventis Pharma Ltd, Dagenham RM10 7XS, Essex, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 23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)00648-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The outcome of oxidative ring expansion/cyclisation of cyclopropanes with a mixed Fe(III)/Cu(II) system was found to be dependent on the mode of cyclisation. When 6-exo cyclisation was attempted unusual products resulting from oxidation of ring opened primary radicals were obtained. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：4651 / 4655

页数：5

共 13 条

[1] A very rapid stereocontrolled entry to highly functionalized [5-8-5] ring systems using the Saegusa reaction
Blake, AJ
Highton, AJ
Majid, TN
Simpkins, NS
[J]. ORGANIC LETTERS, 1999, 1 (11) : 1787 - 1789
[2] Bicyclo[3.3.0]octanone formation by Fe(III) mediated ring expansion transannular cyclisation reactions of cyclopropyl ethers
Booker-Milburn, KI
Dainty, RF
[J]. TETRAHEDRON LETTERS, 1998, 39 (28) : 5097 - 5100
[3] Fe(III) mediated oxidative radical cyclisation of cyclopropanone acetals
Booker-Milburn, KI
Barker, A
Brailsford, W
Cox, B
Mansley, TE
[J]. TETRAHEDRON, 1998, 54 (50) : 15321 - 15344
[4] IRON(III) MEDIATED TRANSFORMATIONS OF CYCLOPROPYLTRIMETHYLSILYL ETHERS .1. FREE-RADICAL TANDEM RING EXPANSION-CYCLIZATION REACTIONS FOR THE RAPID CONSTRUCTION OF [N30] BICYCLIC RING-SYSTEMS
BOOKERMILBURN, KI
THOMPSON, DF
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (18): : 2315 - 2321
[5] OXIDATION AND REDUCTION OF FREE REDICALS BY METAL SALTS
DELAMARE, HE
RUST, FF
KOCHI, JK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (10) : 1437 - &
[6] NEW ANTI-MICROBIAL DITERPENES, DICTYOL-F AND EPIDICTYOL-F, FROM THE BROWN ALGA DICTYOTA-DICHOTOMA
ENOKI, N
TSUZUKI, K
OMURA, S
ISHIDA, R
MATSUMOTO, T
[J]. CHEMISTRY LETTERS, 1983, (10) : 1627 - 1630
[7] FREY B, 1991, SYNLETT, P854
[8] HUMBER DC, 1966, TETRAHEDRON LETT, V41, P4985
[9] SYNTHESIS OF MEDIUM-SIZED BICYCLIC COMPOUNDS BY INTRAMOLECULAR CYCLIZATION OF CYCLIC BETA-KETO RADICALS GENERATED FROM CYCLOPROPANOLS USING MANGANESE(III) TRIS(2-PYRIDINECARBOXYLATE)
IWASAWA, N
FUNAHASHI, M
HAYAKAWA, S
NARASAKA, K
[J]. CHEMISTRY LETTERS, 1993, (03) : 545 - 548
[10] ELECTRON-TRANSFER MECHANISMS FOR ORGANOMETALLIC INTERMEDIATES IN CATALYTIC REACTIONS
KOCHI, JK
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1974, 7 (10) : 351 - 360

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