Construction of an enantiomerically pure 6-substituted 3,5-syn-dihydroxyhexanoic acid system by an enantioselective deprotonation strategy: formal synthesis of an antiobesity agent, (-)-tetrahydrolipstatin.
Preparation of 6-substituted 4-hydroxytetrahydro-2H-pyran-2-one (12), a key intermediate for the synthesis of (-)-tetrahydrolipstatin, was achieved in an optically pure form by employing an enantioselective deprotonation reaction of the prochiral bicyclic derivative (5) as a key step.
Honda
T
T
Faculty of Pharmaceutical Sciences, Hoshi University, Tokyo, Japan. honda@hoshi.ac.jp
Endo
K
K
Ono
S
S
D019440:Anti-Obesity Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002208:Caproates / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D000077403:Orlistat; D011522:Protons; D013057:Spectrum Analysis; D013237:Stereoisomerism
D019440:Anti-Obesity Agents; D002208:Caproates; D007783:Lactones; D011522:Protons; D000077403:Orlistat