An efficient enzymatic preparation of (+)- and (−)-conduritol E, a cyclitol with C2 symmetry

✍ Scribed by Claudia Sanfilippo; Angela Patti; Mario Piattelli; Giovanni Nicolosi

• Book ID: 104361153
• Publisher: Elsevier Science
• Year: 1997
• Tongue: English
• Weight: 292 KB
• Volume: 8
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(97)00129-8

✦ Synopsis

Lypozyme® IM (immobilised lipase from Mucor miehei) catalyses the enantiomeric alcoholysis of tetraacetylconduritol E (_+)-2 to give enantiopure (lR,2R,3R,4R)-tetrahydroxycyclohex-5-ene, (-)-1, and the unreacted ester (1S,2S,3S,4S)tetraacetyloxycyclohex-5-ene, (+)-2. The latter was transformed by basic hydrolysis into (+)-1 in high yield and 95% ee. Selective amination of partial ester (-)-3, obtained by short alcoholysis of (_+)-2, furnished the previously unreported conduramine F-4, (-)-4.