The Synthesis of Desepoxy‐Isotedanolide – A Potential Biosynthetic Precursor of Tedanolide

Abstract

The tedanolides are biologically active polyketides that exhibit a characteristic feature of an 18‐membered macrolactone generated from a primary hydroxyl group. In the realm of polyketides only secondary alcohols are generated by polyketidal transformations. With this knowledge, Taylor hypothesized that the observed macrolactone might arise from an intramolecular transesterification. To investigate this hypothetical transesterification, we completed the synthesis of desepoxy‐isotedanolide as tedanolide's putative biosynthetic precursor. This synthesis required a modified protecting group strategy, which proved to be non‐trivial. Unfortunately, it was not possible to accomplish the envisioned transesterification under laboratory conditions.