Preparation of useful synthetic intermediates of Taxol analogs, cyclooctenone derivatives.
Stereoselective syntheses of omega-(alpha-bromoketo) octanals and nonanal with oxygenated functions and formation of the corresponding eight-membered carbocyclic aldols by subsequent samarium(II)-mediated cyclization are demonstrated. Cyclooctenones deoxygenated at the C2 or C10 position in the taxane framework are prepared by dehydration of the above aldols.
Yamada
K
K
Department of Applied Chemistry, Faculty of Science, Science University of Tokyo, Japan.
Tozawa
T
T
Saitoh
K
K
Mukaiyama
T
T
D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D034242:Cyclooctanes; D003516:Cycloparaffins / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry; D009795:Octanes / Q000737:chemistry; D017239:Paclitaxel / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D012493:Samarium; D013237:Stereoisomerism
D000447:Aldehydes; D034242:Cyclooctanes; D003516:Cycloparaffins; D007659:Ketones; D009795:Octanes; D012493:Samarium; C044494:cyclooctanone; D017239:Paclitaxel; C031639:caprylic aldehyde