Synthetic studies towards d-modified paclitaxel analogues
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 p...
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| Published in: | Journal of the Serbian Chemical Society Vol. 77; no. 11; pp. 1529 - 1539 |
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| Main Authors: | , , |
| Format: | Journal Article |
| Language: | English |
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Serbian Chemical Society
01-01-2012
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| 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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| AbstractList | 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)] |
| Author | Matović Radomir Ferjančić Zorana Saičić Radomir N. |
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| Title | Synthetic studies towards d-modified paclitaxel analogues |
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