Enantioselective deprotonation of meso-cycloheptanone derivative: application to the synthesis of a potential intermediate for pseudomonic acid B.
[reaction: see text] A novel synthetic path to a potential intermediate for the synthesis of pseudomonic acid B was established by employing enantioselective deprotonation of a meso-cycloheptanone derivative bearing hydroxy groups at the 3,4,5,6-positions with lithium (S,S')-alpha,alpha'-dimethyldibenzylamide as a key step.
Honda
Toshio
T
Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan. honda@hoshi.ac.jp
Kimura
Nobuaki
N
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000737:chemistry; D005227:Fatty Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013450:Sulfones
D000894:Anti-Inflammatory Agents, Non-Steroidal; D005227:Fatty Acids; D007783:Lactones; D013450:Sulfones; C116926:rofecoxib; C014246:pseudomonic acid I