Rubrenolide, total synthesis and revision of its reported stereochemical structure

摘要

In this paper the synthesis of the natural product rubrenolide is presented. Due to an error in the original proposed stereochemical structure of rubrenolide, the synthesis was not straightforward. Application of the photo-induced rearrangement of an appropriate epoxy diazomethyl ketone gave access to the precursor lactone with an ee of 91%. Coupling of this lactone with (4S)-2,2-dimethyl-[1,3]-dioxolane4-carbaldehyde gave, after some additional steps, the final product that was identical with an authentic sample of the natural product. (C) 2004 Elsevier Ltd. All rights reserved.