Low-temperature reduction of acyclic (–)-mentholactone derivatives with diisobutylaluminum hydride in methylene chloride

Abstract

Low-temperature treatment of acyclic (-)-mentholactone derivatives with excess diisobutylaluminum hydride in methylene chloride afforded O-isobutyl derivatives of seven-membered lactols. Methyl 6-hydroxy-3,7-dimethyloctanoate behaved similarly to (-)-mentholactone, and its 6-oxo analog, similarly to (-)-mentholactone and isomentholactone.