| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1358905 | Bioorganic & Medicinal Chemistry Letters | 2015 | 4 Pages |
Abstract
(5Z,9Z)-11-Phenylundeca-5,9-dienoic acid was stereoselectively synthesized, based on original cross-cyclomagnesiation of 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2H-pyran and buta-2,3-dien-1-ylbenzene with EtMgBr in the presence of Cp2TiCl2 catalyst giving 2,5-dialkylidenemagnesacyclopentane in 86% yield. The acid hydrolysis of the product and the Jones oxidation of the resulting 2-{[(5Z,9Z)-11-phenylundeca-5,9-dien-1-yl]oxy}tetrahydro-2Н-pyran afforded (5Z,9Z)-11-phenylundeca-5,9-dienoic acid in an overall yield of 75%. A high inhibitory activity of the synthesized acid with respect to human topoisomerase I (hTop1) and II (hTop2α) was determined.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Vladimir A. D’yakonov, Lilya U. Dzhemileva, Aleksey A. Makarov, Alfiya R. Mulukova, Dmitry S. Baev, Elza K. Khusnutdinova, Tatiana G. Tolstikova, Usein M. Dzhemilev,