Synthesis of an Advanced Intermediate of the Jatrophane Diterpene Pl‑4: A Dibromide Coupling Approach

ABSTRACT: The preparation of an advanced intermediate toward the synthesis of the jatrophane diterpene Pl-4 is described. The key step is a regioselective chelation-controlled lithiation of the (Z)-configured bromide in the corresponding vinyl dibromide precursor. The method outlined within this Article is suitable for the facile access of sterically hindered internal vinyl halides for further coupling reactions. A general characteristic of members of the Euphorbiaceae plant family, commonly referred to as spurges, is the milky latex that has been identified as a rich source of structurally complex and intriguing terpene-based natural products. Over the pas