[4+2] Cycloaddition Reactions Between 1,8-Disubstituted Cyclooctatetraenes and Diazo Dienophiles: Stereoelectronic Effects, Anticancer Properties and Application to the Synthesis of 7,8-Substituted Bicyclo[4.2.0] octa-2,4-dienes

被引：8

作者：

Grange, Rebecca L. ^{[1
]}

Gallen, Michael J. ^{[1
]}

Schill, Heiko ^{[1
]}

Johns, Jenny P. ^{[2
]}

Dong, Lin ^{[1
]}

Parsons, Peter G. ^{[2
]}

Reddell, Paul W. ^{[3
]}

Gordon, Victoria A. ^{[3
]}

Bernhardt, Paul V. ^{[1
]}

Williams, Craig M. ^{[1
]}

机构：

[1] Univ Queensland, Sch Chem & Mol Biosci, Brisbane, Qld 4072, Australia

[2] PO Royal Brisbane Hosp, Queensland Inst Med Res, Brisbane, Qld 4029, Australia

[3] EcoBiotics Ltd, Yungaburra, Qld 4884, Australia

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 29期

关键词：

antitumor agents; bicyclo compounds; cycloaddition; cyclooctatetraene; diazo compounds; Diels-Alder reaction; ENDIANDRA-INTRORSA LAURACEAE; A-ACID-G; BIOMIMETIC SYNTHESIS; ORGANIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ORTHO-PHOTOCYCLOADDITION; VALENCE ISOMERIZATION; STEROIDAL 5,7-DIENES; RETRO-CYCLOADDITION; CYCLO-OCTATETRAENES;

D O I：

10.1002/chem.200903454

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A detailed examination of [4+2] cycloaddition reactions between 1,8-disubstituted cyclooctatetraenes and diazo compounds revealed that 4-phenyl-1,2,4-triazole-3,5-dione (PTAD) reacts to form either 2,3- or 3.4-disubstituted adducts. The product distribution can be controlled by modulating the electron density of the cyclooctatetraene. Unprecedented [4+2] cycloadditions between diisopropyl azodicarboxylate (DIAD) and 1,8-disubstituted cyclooctatetraenes are also described and further manipulation of a resulting cycloadduct uncovered a new pathway to the synthetically challenging bicyclo[4.2.0]octa-2,4-diene family. Variation of the substituents resulted in a range of compounds displaying selective action against different human tumour cell types.

引用

页码：8894 / 8903

页数：10

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