Synthetic studies on taxol: highly stereoselective construction of the taxol C-ring via SN2' reduction of an allylic phosphonium salt.
[reaction: see text] The highly stereoselective construction of the C3 stereogenic center of the taxol C-ring is described. The trans isomer at the C3-C8 position of the taxol C-ring, which is required for the total synthesis, as well as its diastereomeric cis isomer were successfully synthesized with highly diastereoselective S(N)2' reduction of the allylic phosphonium salts.
Utsugi
Masayuki
M
Department of Chemistry, Faculty of Science and Engineering, Waseda University, Shinjuku-ku, Tokyo, Japan.
Miyano
Masayuki
M
Nakada
Masahisa
M
D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D017239:Paclitaxel / Q000138:chemical synthesis* / Q000737:chemistry*; D012492:Salts; D013237:Stereoisomerism
D009943:Organophosphorus Compounds; D012492:Salts; D017239:Paclitaxel