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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
http://cer.ihtm.bg.ac.rs/handle/123456789/43
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