ChemInform Abstract: Acid‐Catalyzed Reactions of Sarcophytoxide, a Marine Cembranoid: An Apparently Enantio‐Directive Reaction, Unusual Products and Stereochemical Reconsideration of Epoxide—Ketone Rearrangement.

Abstract

Treatment of sarcophytoxide (I) with perchloric acid affords ketone (+)-III or its antipodal ketone (-)-III depending on the reaction time. This curious phenomenon is interpreted by assuming the epimerization of the doubly allylic C-O linkage at C-2 of starting cembranoid (I). -(NII, K.; TAGAMI, K.; KIJIMA, M.; MUNAKATA, T.; OOI, T.; KUSUMI*, T.; Bull. Chem.