synthetic studies towards d-modified paclitaxel analogues

synthetic studies towards d-modified paclitaxel analogues

;Matović Radomir;Saičić Radomir N.;Ferjančić Zorana
meditsinskaia radiologiia 2012 Vol. 77 pp. 1529-1539
154
radomir2012journalsynthetic

Abstract

A synthetic sequence has been developed for the preparation of 9,10-O-diacetyl-4-desmethylene-4β-(3-butenyl)-4α-hydroxy-5-O-mesyltaxicin I-1,2-carbonate 3, an intermediate in the attempted synthesis of cyclobutane paclitaxel analogue. A series of reactions of 3 has been investigated, including the protection of sterically hindered C-4α hydroxy group and oxidative cleavage of the terminal double bond. Cyclization of 13 to the cyclobutane-containing intermediate failed due to unexpected instability of the DMS protecting group under basic conditions. [Acknowledgments. Financial support of the Ministry of Education and Science of the Republic of Serbia is acknowledged (Project No. 172027)]

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