Molecular structure of paclitaxel.Crystal structure of paclitaxel.
Paclitaxel total synthesis in organic chemistry is a major ongoing research effort in the total synthesis of paclitaxel (Taxol).[1] This diterpenoid is an important drug in the treatment of cancer but, also expensive because the compound is harvested from a scarce resource, namely the Pacific yew (Taxus brevifolia). Not only is the synthetic reproduction of the compound itself of great commercial and scientific importance, but it also opens the way to paclitaxel derivatives not found in nature but with greater potential.
The paclitaxel molecule consists of a tetracyclic core called baccatin III and an amide tail. The core rings are conveniently called (from left to right) ring A (a cyclohexene), ring B (a cyclooctane), ring C (a cyclohexane) and ring D (an oxetane).
The paclitaxel drug development process took over 40 years. The anti-tumor activity of a bark extract of the Pacific yew tree was discovered in 1963 as a follow-up of a US government plant screening program already in existence 20 years before that. The active substance responsible for the anti-tumor activity was discovered in 1969 and structure elucidation was completed in 1971. Robert A. Holton of Florida State University succeeded in the total synthesis of paclitaxel in 1994, a project that he had started in 1982. In 1989 Holton had also developed a semisynthetic route to paclitaxel starting from 10-deacetylbaccatin III. This compound is a biosynthetic precursor and is found in larger quantities than paclitaxel itself in Taxus baccata (the european yew). In 1990
Bristol-Myers Squibb bought a licence to the patent for this process which in the years to follow earned Florida State University and Holton (with a 40% take) over 200 million US dollars.
^Note that the original publications about the total synthesis use the name "taxol", which used to be the generic name before it was accepted as a trademark in 1992.
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Paclitaxeltotalsynthesis in organic chemistry is a major ongoing research effort in the totalsynthesis of paclitaxel (Taxol). This diterpenoid is an...
surrounding [paclitaxel] and [the Pacific yew] in the early 1990s ... helped bolster [a] link between totalsynthesis and the [paclitaxel] supply problem...
The synthesis makes use of various protecting groups as follows: Paclitaxeltotalsynthesis Danishefsky Taxol totalsynthesis Holton Taxol total synthesis...
of Taxol (generic name: paclitaxel). The Holton Taxol totalsynthesis is a good example of a linear synthesis. The synthesis starts from patchoulene oxide...
synthesis makes use of various protecting groups as follows: Paclitaxeltotalsynthesis Holton Taxol totalsynthesis Kuwajima Taxol totalsynthesis Mukaiyama...
Natural products can also be prepared by chemical synthesis (both semisynthesis and totalsynthesis) and have played a central role in the development...
produced by totalsynthesis from simple starting materials. Semisynthesis is a means of preparing many medicines more cheaply than by totalsynthesis since...
than most alternatives. Chiral pool synthesis is used to build a part of epothilone (an alternative to paclitaxel) from readily available enantiopure...
as toxic to cancer cells as the anticancer drug taxol”, also known as Paclitaxel, a prevalent chemotherapy medication. As such, theoretically, only an...
paclitaxel. Discodermolide was recognized as one of the most potent natural promoters of tubulin assembly. A large number of efforts toward the total...
for paclitaxel which can affect cardiac function and cause severe hypersensitivity) are not needed. Endotoxin-like properties known from paclitaxel, like...
analgesia, in part because the nerve endings die from calcium overload. A totalsynthesis of (+)-resiniferatoxin was completed by the Paul Wender group at Stanford...
macrophages and other tissues. CYP27A1 contributes significantly to total bile acid synthesis by catalyzing sterol side chain oxidation, after which cleavage...
and most organic solvents, specifically hydrocarbons and alcohols. A totalsynthesis of the compound was reported in 1965; that procedure called for the...
industry. Some steroidal hormones are economically obtained only by totalsynthesis from petrochemicals (e.g. 13-alkyl steroids). For example, the pharmaceutical...
a complex, terpenoid natural product, related to but simpler than the paclitaxel that follows, which displays a complex ring structure including 3-, 5-...
severe adverse effects. Docetaxel and paclitaxel have comparable efficacy metastatic breast cancer but paclitaxel has less severe side effects. Additionally...
chiral totalsynthesis of compactin". J. Am. Chem. Soc. 104 (15): 4251–4253. doi:10.1021/ja00379a037. Hirama M, Iwashita M (1983). "Synthesis of (+)-Mevinolin...
predominant component has long been of interest. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol...
least thirty separate groups were working on the totalsynthesis of the chemotherapy medicine paclitaxel (Taxol), culminating with the groups of Robert...
The TotalSynthesis of Natural Products. Vol. 10. New York: John Wiley & Sons. pp. 90–6. ISBN 978-0-470-12962-3. Schmid G, Hofheinz W (1983). "Total Synthesis...
DE, Au-Yeung BW, et al. (June 1981). "Asymmetric TotalSynthesis of Erythromycin. 3. TotalSynthesis of Erythromycin". Journal of the American Chemical...
Gold nanoparticles are being investigated as carriers for drugs such as Paclitaxel. The administration of hydrophobic drugs require molecular encapsulation...
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