Synthesis of the first fluorinated cantharidin analogues

被引：45

作者：

Essers, M ^{[1
]}

Wibbeling, B ^{[1
]}

Haufe, G ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 32期

关键词：

Diels-Alder reaction; fluorinated cantharidin analogues; fluorinated maleic anhydrides; furan; O-17; NMR;

D O I：

10.1016/S0040-4039(01)01056-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fluorinated cantharidin analogues (4-7) have been synthesized for the first time. The key step in each synthesis is an exo-selective Diels-Alder reaction of furan with the appropriate fluorinated maleic anhydride. O-17 NMR measurements of 5-7 and the corresponding non-fluorinated parent compounds were undertaken to show the influence of the fluorine substituent(s) on the electronic properties of the oxygen atoms. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：5429 / 5433

页数：5

共 53 条

[1] S-33 AND O-17 NMR-STUDIES OF SULFOLANE IN ACETIC-ACID AND RELATED SOLVENTS
ALI, AAM
HARRIS, RK
BELTON, PS
[J]. MAGNETIC RESONANCE IN CHEMISTRY, 1990, 28 (04) : 318 - 323
[2] TANDEM CYCLOADDITION-ENZYMATIC TRANSESTERIFICATION - AN ENANTIOSELECTIVE DIELS-ALDER REACTION EQUIVALENT
ANDREU, C
MARCO, JA
ASENSIO, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11): : 3209 - 3210
[3] Diels-Alder reactions of polyfluorinated 2,4-cyclohexadienones with α- and β-fluorostyrenes
Bogachev, AA
Kobrina, LS
Meyer, OCJ
Haufe, G
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1999, 97 (1-2) : 135 - 143
[4] NATURAL ABUNDANCE O-17 NMR-STUDY OF ALPHA-SUBSTITUTED METHYL ACETATES
BOYKIN, DW
SUBRAMANIAN, TS
BAUMSTARK, AL
[J]. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 1989, 45 (03): : 335 - 338
[5] O-17 NMR-SPECTROSCOPY - STUDY OF INTRAMOLECULAR HYDROGEN-BONDING IN PHENOLS AND SALICYLALDEHYDES
BOYKIN, DW
CHANDRASEKARAN, S
BAUMSTARK, AL
[J]. MAGNETIC RESONANCE IN CHEMISTRY, 1993, 31 (05) : 489 - 494
[6] BUDDRUS J, 1966, TETRAHEDRON LETT, P5379
[7] CAVILL GW, 1971, NATURALLY OCCURRING
[8] Cycloaddition reactions of furan derivatives with trifluoroethene
Chambers, RD
Gilbert, AF
Powell, RL
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2000, 104 (02) : 233 - 237
[9] O-17 NUCLEAR MAGNETIC-RESONANCE .1. ALCOHOLS
CRANDALL, JK
CENTENO, MA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (07) : 1183 - 1184
[10] Total synthesis of (-)-palasonin and (+)-palasonin and related chemistry
Dauben, WG
Lam, JYL
Guo, ZR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) : 4816 - 4819

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