Journal
STEROIDS
Volume 102, Issue -, Pages 110-117Publisher
ELSEVIER SCIENCE INC
DOI: 10.1016/j.steroids.2015.08.006
Keywords
Cross-cyclomagnesiation; 5Z,9Z-dienoic acids; Titanocene dichloride; Grignard reagents; Magnesacyclopentane; Dzhemilev reaction; Topoisomerase I inhibitors
Funding
- Russian Science Foundation [14-13-00263]
- Russian Science Foundation [14-13-00263] Funding Source: Russian Science Foundation
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Two approaches to stereoselective synthesis of steroid 5Z,9Z-dienoic acids were developed, the first one being based on the cross-cyclomagnesiation of 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2H-pyran and 1,2-diene cholesterol derivatives on treatment with EtMgBr catalyzed by Cp2TiCl2, while the other involving the synthesis of esters of hydroxy steroids with (5Z,9Z)-tetradeca-5,9-dienedioic acid, prepared in two steps using homo-cyclomagnesiation of 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2H-pyran as the key step. High inhibitory activity of the synthesized acids against human topoisomerase I (hTop1) was found. (C) 2015 Published by Elsevier Inc.
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