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An efficient semisynthesis of 7-deoxypaclitaxel from taxine

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2000
Authors
Saičić, Radomir N.
Matović, Radomir
Article (Published version)
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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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4
11
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/43
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  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - 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 . .

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