SYNTHESIS AND TRANSFORMATIONS OF METALLACYCLES. 45. CROSS-CYCLOMAGNESIATION OF 1,2-DIENES IN THE SYNTHESIS OF 5Z, 9Z-DIENOIC ACIDS, EFFICIENT INHIBITORS OF HUMAN TOPOISOMERASE I

D’yakonov, V.A.; Dzhemileva, L.U.; Makarov, A.A.; Mulyukova, A.R.; Tuktarova, R.A.; Islamov, I.I.; Dzhemileva, U.M.

SYNTHESIS AND TRANSFORMATIONS OF METALLACYCLES. 45. CROSS-CYCLOMAGNESIATION OF 1,2-DIENES IN THE SYNTHESIS OF 5Z, 9Z-DIENOIC ACIDS, EFFICIENT INHIBITORS OF HUMAN TOPOISOMERASE I

Publication date: 2015

Abstract:

An original method for the synthesis of natural and synthetic 5Z,9Z-dienoic acids with high selectivity (>98%) and ~50% yields was elaborated. The method is based on a new Cp2TiCl2catalyzed cross-cyclomagnesiation reaction of terminal aliphatic and O-containing 1,2-dienes using Grignard reagents. The synthesized acids exhibited in vitro high inhibiting activity against human topoisomerase I.

Keywords:
cyclomagnesiation, 1,2-dienes, magnesacyclopentane, 5Z,9Z-dienoic acids, titanocene dichloride, topoisomerase I

Тип: Article

DOI 10.1007/s11172-015-1128-7

SYNTHESIS AND TRANSFORMATIONS OF METALLACYCLES. 45. CROSS-CYCLOMAGNESIATION OF 1,2-DIENES IN THE SYNTHESIS OF 5Z, 9Z-DIENOIC ACIDS, EFFICIENT INHIBITORS OF HUMAN TOPOISOMERASE I

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