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 precursor of taxol.
Doi
Takayuki
T
Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan.
Fuse
Shinichiro
S
Miyamoto
Shigeru
S
Nakai
Kazuoki
K
Sasuga
Daisuke
D
Takahashi
Takashi
T
D000470:Alkaloids / Q000737:chemistry; D000972:Antineoplastic Agents, Phytogenic / Q000494:pharmacology*; D001331:Automation; D002498:Centrifugation; D002626:Chemistry, Pharmaceutical / Q000295:instrumentation* / Q000379:methods*; D003201:Computers; D005374:Filtration; D008872:Microwaves; D008956:Models, Chemical; D015394:Molecular Structure; D017239:Paclitaxel / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D043823:Taxoids / Q000737:chemistry; D013678:Technology, Pharmaceutical / Q000295:instrumentation* / Q000379:methods*; D013696:Temperature; D013997:Time Factors
D000470:Alkaloids; D000972:Antineoplastic Agents, Phytogenic; D043823:Taxoids; C073950:baccatin III; D017239:Paclitaxel