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
TY - JOUR
AU - Saičić, Radomir N.
AU - Matović, Radomir
PY - 2000
UR - http://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",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/43",
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 RN, Matović R. An efficient semisynthesis of 7-deoxypaclitaxel from taxine. Journal of the Chemical Society, Perkin Transactions 1. 2000;(1):59-65
Saičić, R. N.,& Matović, R. (2000). An efficient semisynthesis of 7-deoxypaclitaxel from taxine.
Journal of the Chemical Society, Perkin Transactions 1(1), 59-65.
https://doi.org/10.1039/a907288h
Saičić Radomir N., Matović Radomir, "An efficient semisynthesis of 7-deoxypaclitaxel from taxine", no. 1 (2000):59-65,
https://doi.org/10.1039/a907288h .
