A COBALOXIME-MEDIATED RADICAL ROUTE TO BUTENOLIDES

被引：13

作者：

BRANCHAUD, BP

SLADE, RM

JANISSE, SK

机构：

[1] Department of Chemistry, University of Oregon, Eugene

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 49期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(00)61501-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photolysis of alkyl cobaloximes with maleic anhydride and PhSSPh proceeds via radical alkene addition and subsequent PhSSPh trapping. The product trans 3-phenylthio 4-alkyl succinic anhydrides can be converted by oxidation and thermal syn elimination into 3-substituted maleic anhydrides, which are known to be regioselectively and chemoselectively reduced to produce gamma-hydroxybutenolides or butenolides.

引用

页码：7885 / 7888

页数：4

共 48 条

[1] CASCADE COBALT GROUP TRANSFER - RADICAL TRAPPING - TANDEM RADICAL CYCLIZATION REACTIONS IN SYNTHESIS
ALI, A
HARROWVEN, DC
PATTENDEN, G
[J]. TETRAHEDRON LETTERS, 1992, 33 (20) : 2851 - 2854
[2] DIRECT RING EXPANSION OF PENICILLINS TO 3-EXOMETHYLENE CEPHALOSPORINS
BALDWIN, JE
ADLINGTON, RM
KANG, TW
[J]. TETRAHEDRON LETTERS, 1991, 32 (48) : 7093 - 7096
[3] ENANTIOSELECTIVE SYNTHESIS OF KAINOID ANALOGS BY COBALT-MEDIATED CYCLIZATIONS
BALDWIN, JE
MOLONEY, MG
PARSONS, AF
[J]. TETRAHEDRON, 1991, 47 (01) : 155 - 172
[4] AN INTRAMOLECULAR COBALT CYCLIZATION FOR THE CONSTRUCTION OF SUBSTITUTED PYRROLIDINES
BALDWIN, JE
MOLONEY, MG
PARSONS, AF
[J]. TETRAHEDRON, 1992, 48 (42) : 9373 - 9384
[5] ENANTIOSELECTIVE KAINOID SYNTHESIS BY COBALT-MEDIATED CYCLIZATION OF AN AMINO-ACID DERIVATIVE
BALDWIN, JE
MOLONEY, MG
PARSONS, AF
[J]. TETRAHEDRON, 1990, 46 (20) : 7263 - 7282
[6] TANDEM NUCLEOPHILIC AND RADICAL CHEMISTRY IN THE REPLACEMENT OF THE HYDROXYL GROUP BY A CARBON CARBON BOND - A CONCISE SYNTHESIS OF SHOWDOMYCIN
BARTON, DHR
RAMESH, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) : 891 - 892
[7] BEGLEY MJ, 1975, TETRAHEDRON LETT, V48, P4279
[8] BOURGUIGNON JJ, 1987, J ORG CHEM, V52, P4788
[9] NEW SYNTHETIC METHODS VIA FREE-RADICALS - FREE-RADICAL GENERATION VIA PHOTOLYTIC HOMOLYSIS OF ALKYL-COBALOXIME C-CO BONDS - EFFICIENT RADICAL TRAPPING WITH USEFUL FUNCTIONAL-GROUPS
BRANCHAUD, BP
MEIER, MS
MALEKZADEH, MN
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (02) : 212 - 217
[10] STEREOELECTRONIC CONTROL OF ELECTRON-TRANSFER IN THE OXIDATIVE ADDITION OF [PY(DMGH)2COI]-NA+ TO CARBOHYDRATE SECONDARY IODIDES
BRANCHAUD, BP
YU, GX
[J]. ORGANOMETALLICS, 1991, 10 (11) : 3795 - 3797

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