Construction of the tetracyclic ring system of diterpene alkaloids via cationic [5 + 2] cycloaddition

Org Biomol Chem. 2023 Jun 7;21(22):4587-4590. doi: 10.1039/d3ob00647f.

Abstract

The ABCD ring system of C18/C19 diterpene alkaloids was constructed via cationic [5 + 2] cycloaddition to forge a bicyclo[3.2.1]octane, an intramolecular aldol reaction to form a seven-membered ring, oxidation of a phenol at the para-position, and introduction of a one-carbon unit via Stille coupling followed by oxidative cleavage of a furan ring.