- SEMI-SYNTHETIC ROUTE FOR THE PREPARATION OF PACLITAXEL, DOCETAXEL, AND 10-DEACETYLBACCATIN III FROM 9-DIHYDRO-13-ACETYLBACCATIN III
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A novel semisynthetic route has been provided in the preparation of docetaxel and paclitaxel. This new process involves the conversion of 9-dihydro-13-acetylbaccatinIII to docetaxel and paclitaxel by the step of converting 9-dihydro-13-acetylbaccatin III into 7-O-triethylsilyl-9,10-diketobaccatin III, and adding docetaxel and paclitaxel side chain precursors, respectively, to form a new class of taxane intermediates, such as 7-O-triethylsilyl-9,10-diketodocetaxel and 7-O-triethylsilyl-9,10-diketopaclitaxeltaxel. These new intermediates then by a series reduction, acetylation of the 10-hydroxyl position for paclitaxel and finally deprotection to yield docetaxel and paclitaxel, the most important anti-cancer drugs.
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Page/Page column 8
(2008/06/13)
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- Beta-Lactams useful for preparation of substituted isoserine esters using metal alkoxides
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β-lactams are disclosed which are useful for preparing N-acyl, N-sulfonyl and N-phosphoryl substituted esters by reaction with a metal alkoxide.
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- Total synthesis of Taxol. 1. Retrosynthesis, degradation, and reconstitution
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A successful strategy for the enantioselective synthesis of the natural stereoisomer of Taxol (1) has been developed. This strategy utilized the convergent assembly of Taxol's central eight-membered B ring from preformed synthons for rings A (10) and C (9) followed by late introduction of the D ring and side chain. Degradative studies confirmed the viability of certain crucial manipulations including oxidation of the C13 position (35 → 3) and regioselective introduction of the C1-hydroxyl, C2-benzoyloxy moiety (29 → 31). Additionally, a convenient method for the large-scale production of 29, a derivative useful for C2 analog production, was developed.
- Nicolaou,Nantermet,Ueno,Guy,Couladouros,Sorensen
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p. 624 - 633
(2007/10/02)
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- Semi-synthesis of taxane derivatives using metal alkoxides and oxazinones
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A process for preparing taxane derivatives taxol by providing a metal alkoxide having the bi, tri-, or tetracyclic taxane nucleus, reacting the metal alkoxide with an oxazinone to form an intermediate, and converting the intermediate to the taxane derivative.
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