An efficient semisynthesis of 7-deoxypaclitaxel from taxine
Abstract
A semisynthesis of 7-deoxypaclitaxel 4 is described, starting from taxine 6 - the most abundant naturally occurring taxane diterpene fraction. A key step in this transformation is a tandem reaction: stereoselective osmylation of cinnamic ester 14/intramolecularly assisted methanolysis of 16, which gives the key intermediate 5, along with the optically pure ester 17 - a precursor for the synthesis of the paclitaxel side-chain. In this way, the cinnamoyltaxicine 9 is converted into 7-deoxybaccatin III 25 in 11 steps, and in 15% overall yield.
Source:
Journal of the Chemical Society, Perkin Transactions 1, 2000, 1, 59-65
DOI: 10.1039/a907288h
ISSN: 1470-4358
WoS: 000084864000008
Scopus: 2-s2.0-52549119999
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IHTMTY - JOUR AU - Saičić, Radomir N. AU - Matović, Radomir PY - 2000 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/43 AB - A semisynthesis of 7-deoxypaclitaxel 4 is described, starting from taxine 6 - the most abundant naturally occurring taxane diterpene fraction. A key step in this transformation is a tandem reaction: stereoselective osmylation of cinnamic ester 14/intramolecularly assisted methanolysis of 16, which gives the key intermediate 5, along with the optically pure ester 17 - a precursor for the synthesis of the paclitaxel side-chain. In this way, the cinnamoyltaxicine 9 is converted into 7-deoxybaccatin III 25 in 11 steps, and in 15% overall yield. T2 - Journal of the Chemical Society, Perkin Transactions 1 T1 - An efficient semisynthesis of 7-deoxypaclitaxel from taxine IS - 1 SP - 59 EP - 65 DO - 10.1039/a907288h ER -
@article{ author = "Saičić, Radomir N. and Matović, Radomir", year = "2000", abstract = "A semisynthesis of 7-deoxypaclitaxel 4 is described, starting from taxine 6 - the most abundant naturally occurring taxane diterpene fraction. A key step in this transformation is a tandem reaction: stereoselective osmylation of cinnamic ester 14/intramolecularly assisted methanolysis of 16, which gives the key intermediate 5, along with the optically pure ester 17 - a precursor for the synthesis of the paclitaxel side-chain. In this way, the cinnamoyltaxicine 9 is converted into 7-deoxybaccatin III 25 in 11 steps, and in 15% overall yield.", journal = "Journal of the Chemical Society, Perkin Transactions 1", title = "An efficient semisynthesis of 7-deoxypaclitaxel from taxine", number = "1", pages = "59-65", doi = "10.1039/a907288h" }
Saičić, R. N.,& Matović, R.. (2000). An efficient semisynthesis of 7-deoxypaclitaxel from taxine. in Journal of the Chemical Society, Perkin Transactions 1(1), 59-65. https://doi.org/10.1039/a907288h
Saičić RN, Matović R. An efficient semisynthesis of 7-deoxypaclitaxel from taxine. in Journal of the Chemical Society, Perkin Transactions 1. 2000;(1):59-65. doi:10.1039/a907288h .
Saičić, Radomir N., Matović, Radomir, "An efficient semisynthesis of 7-deoxypaclitaxel from taxine" in Journal of the Chemical Society, Perkin Transactions 1, no. 1 (2000):59-65, https://doi.org/10.1039/a907288h . .