SYNTHESIS OF OXACYCLIC CARBOXYLIC ESTERS THROUGH RING-CLOSURE OF ALPHA-ALKOXY ESTER FREE-RADICALS

被引:32
作者
LOLKEMA, LDM [1 ]
HIEMSTRA, H [1 ]
ALGHOUCH, AA [1 ]
SPECKAMP, WN [1 ]
机构
[1] UNIV AMSTERDAM,DEPT ORGAN CHEM,NIEUWE ACHTERGRACHT 129,1018 WS AMSTERDAM,NETHERLANDS
关键词
D O I
10.1016/0040-4039(91)80366-E
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cyclizations of 1-methoxycarbonyl-2-oxa-5-hexenyl (and related) radical intermediates, generated from phenylthio precursors, proceed in good yields and mainly lead to substituted 2-tetrahydrofurancarboxylic esters.
引用
收藏
页码:1491 / 1494
页数:4
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共 27 条
[11]   C-13 NMR-SPECTRA OF SATURATED HETEROCYCLES .11. TETRAHYDROPYRANS (OXANES) [J].
ELIEL, EL ;
MANOHARAN, M ;
PIETRUSIEWICZ, KM ;
HARGRAVE, KD .
ORGANIC MAGNETIC RESONANCE, 1983, 21 (02) :94-106
[12]  
Esch PM, 1989, SYNLETT, P38
[13]   SYNTHESIS OF CYCLIC ALPHA-AMINO-ACIDS THROUGH RING-CLOSURE OF GLYCINE DERIVED FREE-RADICALS [J].
ESCH, PM ;
HIEMSTRA, H ;
SPECKAMP, WN .
TETRAHEDRON LETTERS, 1990, 31 (05) :759-762
[14]   THE SYNTHESIS OF SUBSTITUTED LACTONES BY INTRAMOLECULAR CHIRALITY TRANSFER WITH STEREODIFFERENTIATING CHIRAL ALPHA-ESTER RADICAL INTERMEDIATES [J].
HANESSIAN, S ;
DIFABIO, R ;
MARCOUX, JF ;
PRUDHOMME, M .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3436-3438
[15]   STEREOSELECTIVE TANDEM RADICAL CYCLIZATIONS - SYNTHESIS OF ISOIRIDOMYRMECIN [J].
KILBURN, JD .
TETRAHEDRON LETTERS, 1990, 31 (15) :2193-2196
[16]   CHIRALITY TRANSMISSION INVOLVING A FREE-RADICAL-MEDIATED 6-EXO CYCLIZATION PROCESS - STEREOCONTROLLED SYNTHESIS OF BRANCHED-CHAIN 1,4-DIOLS [J].
KOREEDA, M ;
HAMANN, LG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8175-8177
[17]   SYNTHESIS OF OXACYCLIC CARBOXYLIC ESTERS BY WAY OF METHOXYCARBONYLOXONIUM IONS - EVIDENCE FOR A CATIONIC OXA-COPE REARRANGEMENT [J].
LOLKEMA, LDM ;
HIEMSTRA, H ;
MOOIWEER, HH ;
SPECKAMP, WN .
TETRAHEDRON LETTERS, 1988, 29 (48) :6365-6368
[18]   CYCLO-ADDITIONS OF 3-METHOXYFURAN WITH MONO-ACTIVATED DIENOPHILES - APPLICATION TO THE SYNTHESIS OF (+/)-AVENACIOLIDES [J].
MURAI, A ;
TAKAHASHI, K ;
TAKETSURU, H ;
MASAMUNE, T .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (05) :221-222
[19]   NUCLEOPHILIC ADDITIONS TO THIONOLACTONES - NEW SYNTHETIC TECHNOLOGY FOR THE CONSTRUCTION OF MEDIUM-RING AND LARGE-RING ETHERS [J].
NICOLAOU, KC ;
MCGARRY, DG ;
SOMERS, PK ;
VEALE, CA ;
FURST, GT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (08) :2504-2506
[20]   RAPID CHROMATOGRAPHIC TECHNIQUE FOR PREPARATIVE SEPARATIONS WITH MODERATE RESOLUTION [J].
STILL, WC ;
KAHN, M ;
MITRA, A .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (14) :2923-2925