A Formal Total Synthesis of Taxol Aided by an Automated Synthesizer

A 36‐step synthesis was carried out in automated synthesizers to provide a synthetic key intermediate of taxol. A key step involved a microwave‐assisted alkylation reaction to construct the ABC ring system from an AC precursor. Subsequent formation of the D ring afforded baccatin III, a well‐known p...

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Bibliographic Details
Published in:Chemistry, an Asian journal an Asian journal, 2006-09, Vol.1 (3), p.370-383
Main Authors: Doi, Takayuki, Fuse, Shinichiro, Miyamoto, Shigeru, Nakai, Kazuoki, Sasuga, Daisuke, Takahashi, Takashi
Format: Article
Language:English
Subjects:
Alkaloids - chemistry
Antineoplastic Agents, Phytogenic - pharmacology
antitumor agents
automated synthesis
Automation
Centrifugation
Chemistry, Pharmaceutical - instrumentation
Chemistry, Pharmaceutical - methods
Computers
Filtration
Microwaves
Models, Chemical
Molecular Structure
natural products
Paclitaxel - chemical synthesis
Paclitaxel - chemistry
Stereoisomerism
synthetic methods
Taxoids - chemistry
Technology, Pharmaceutical - instrumentation
Technology, Pharmaceutical - methods
Temperature
Time Factors
total synthesis
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Summary:A 36‐step synthesis was carried out in automated synthesizers to provide a synthetic key intermediate of taxol. A key step involved a microwave‐assisted alkylation reaction to construct the ABC ring system from an AC precursor. Subsequent formation of the D ring afforded baccatin III, a well‐known precursor of taxol. A Konzerted effort: A 36‐step synthesis was carried out by using automated synthesizers (ChemKonzert shown in the background) to provide a key intermediate of taxol. A crucial step was a microwave‐assisted alkylation to convert an AC construct into the ABC ring system. Formation of the D ring afforded baccatin III (see structure), a well‐known precursor of taxol.
ISSN:1861-4728
1861-471X
DOI:10.1002/asia.200600156