Lipase catalyzed desymmetrization of roof shape cis-11,12-bis(hydroxymethyl)-9,10-dihydro-9,10-ethanoanthracene

Abstract

Biocatalyzed desymmetrization of roof shape meso cis-11,12-bis(hydroxymethyl)-9,10-dihydro-9,10-ethanoanthracene has been achieved. The absolute configuration of the product is established by single crystal X-ray analysis of its diastereomer prepared with R-chloropropionic acid. Single crystal analysis of the chiral roof shape monoacetate shows a P-helical motif due to the extended intramolecular hydrogen bonding while the racemic sample exhibits intermolecular double hydrogen bonding holding two molecules together as a dimmer.