Efficient synthesis of (±)-, (+)-, and (-)-conduritol C via palladium(II)-catalyzed 1,4,-diacetoxylation in combination with enzymatic hydrolysis

Palladium-catalyzed diacetoxylation of 5,6-isopropylendioxy-1,3-cyclohexadiene (3) was stereoselective and gave the trans-diacetate 4 (>94% trans), which after hydrolysis and deprotection, afforded (+/-)-conduritol. Enzymatic hydrolysis of diacetate 4 produced enantiomerically pure diol (-)-5 (>99.5% ee) and enantiomerically pure (+)-4 (>99.5% ee). Compounds (-)-5 and (1)-4 were subsequently transformed to (-)- and (+)-conduritol C, respectively.