A synthetic sequence has been developed for the preparation of 9,10- di-O-diacetyl-4-desmethylene-4β-(3-butenyl)-4α-hydroxy-5-O-mesyltaxicin I- -1,2-carbonate 3, an intermediate in an attempted synthesis of a cyclobutane paclitaxel analogue. A series of reactions of 3 were investigated, including the protection of the sterically hindered C-4α-hydroxy group and the oxidative cleavage of the terminal double bond. Cyclization of 13 to the cyclobutane-containing intermediate failed due to the unexpected instability of the dimethylsilane protecting group under basic conditions.
Razvijena je sintetička sekvenca za dobijanje 9,10-di-O-acetil-4-desmetilen-4β-(3-butenil)-4α-hidroksi-5-O-meziltaksicin I-1,2-karbonata (3), intermedijera u pokušanoj sintezi ciklobutanskog analoga paklitaksela. Ispitivana je mogućnost dalje hemijske transformacije jedinjenja 3, kao što je zaštita sterno izrazito zaštićene C-4α hidroksilne grupe i oksidativna fragmentacija terminalne dvostruke veze. Ciklizacija jedinjenja 13 nije dala željeni rezultat - intermedijer sa ciklobutanovim prstenom, što je posledica neočekivane nestabilnosti DMS-zaštitne grupe u baznim reakcionim uslovima.
TY - JOUR
AU - Ferjančić, Zorana
AU - Matović, Radomir
AU - Saičić, Radomir N.
PY - 2012
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1056
AB - A synthetic sequence has been developed for the preparation of 9,10- di-O-diacetyl-4-desmethylene-4β-(3-butenyl)-4α-hydroxy-5-O-mesyltaxicin I- -1,2-carbonate 3, an intermediate in an attempted synthesis of a cyclobutane paclitaxel analogue. A series of reactions of 3 were investigated, including the protection of the sterically hindered C-4α-hydroxy group and the oxidative cleavage of the terminal double bond. Cyclization of 13 to the cyclobutane-containing intermediate failed due to the unexpected instability of the dimethylsilane protecting group under basic conditions.
AB - Razvijena je sintetička sekvenca za dobijanje 9,10-di-O-acetil-4-desmetilen-4β-(3-butenil)-4α-hidroksi-5-O-meziltaksicin I-1,2-karbonata (3), intermedijera u pokušanoj sintezi ciklobutanskog analoga paklitaksela. Ispitivana je mogućnost dalje hemijske transformacije jedinjenja 3, kao što je zaštita sterno izrazito zaštićene C-4α hidroksilne grupe i oksidativna fragmentacija terminalne dvostruke veze. Ciklizacija jedinjenja 13 nije dala željeni rezultat - intermedijer sa ciklobutanovim prstenom, što je posledica neočekivane nestabilnosti DMS-zaštitne grupe u baznim reakcionim uslovima.
PB - Serbian Chemical Soc, Belgrade
T2 - Journal of the Serbian Chemical Society
T1 - Synthetic studies towards D-modified paclitaxel analogues
T1 - Sintetičke studije analoga paklitaksela sa modifikovanim D-prstenom
VL - 77
IS - 11
SP - 1529
EP - 1539
DO - 10.2298/JSC120626094F
ER -
@article{
author = "Ferjančić, Zorana and Matović, Radomir and Saičić, Radomir N.",
year = "2012",
abstract = "A synthetic sequence has been developed for the preparation of 9,10- di-O-diacetyl-4-desmethylene-4β-(3-butenyl)-4α-hydroxy-5-O-mesyltaxicin I- -1,2-carbonate 3, an intermediate in an attempted synthesis of a cyclobutane paclitaxel analogue. A series of reactions of 3 were investigated, including the protection of the sterically hindered C-4α-hydroxy group and the oxidative cleavage of the terminal double bond. Cyclization of 13 to the cyclobutane-containing intermediate failed due to the unexpected instability of the dimethylsilane protecting group under basic conditions., Razvijena je sintetička sekvenca za dobijanje 9,10-di-O-acetil-4-desmetilen-4β-(3-butenil)-4α-hidroksi-5-O-meziltaksicin I-1,2-karbonata (3), intermedijera u pokušanoj sintezi ciklobutanskog analoga paklitaksela. Ispitivana je mogućnost dalje hemijske transformacije jedinjenja 3, kao što je zaštita sterno izrazito zaštićene C-4α hidroksilne grupe i oksidativna fragmentacija terminalne dvostruke veze. Ciklizacija jedinjenja 13 nije dala željeni rezultat - intermedijer sa ciklobutanovim prstenom, što je posledica neočekivane nestabilnosti DMS-zaštitne grupe u baznim reakcionim uslovima.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Synthetic studies towards D-modified paclitaxel analogues, Sintetičke studije analoga paklitaksela sa modifikovanim D-prstenom",
volume = "77",
number = "11",
pages = "1529-1539",
doi = "10.2298/JSC120626094F"
}
Ferjančić, Z., Matović, R.,& Saičić, R. N.. (2012). Synthetic studies towards D-modified paclitaxel analogues. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 77(11), 1529-1539.
https://doi.org/10.2298/JSC120626094F
Ferjančić Z, Matović R, Saičić RN. Synthetic studies towards D-modified paclitaxel analogues. in Journal of the Serbian Chemical Society. 2012;77(11):1529-1539.
doi:10.2298/JSC120626094F .
Ferjančić, Zorana, Matović, Radomir, Saičić, Radomir N., "Synthetic studies towards D-modified paclitaxel analogues" in Journal of the Serbian Chemical Society, 77, no. 11 (2012):1529-1539,
https://doi.org/10.2298/JSC120626094F . .
