Polycyclic polyprenylated acylphloroglucinols (PPAPs) are a family of meroterpenoids with fascinating and complex chemical structures. Due to a wide range of intriguing biological activities, PPAPs represent potential lead structures for neuroscience, infectious disease, and oncology drug discovery programs. Thus, several synthetic approaches, some of which culminated in elegant total syntheses, have been devised. The most prominent congener, the neuroactive hyperforin (1), is one of the main bioactive compounds in Hypericum perforatum (St. John's wort) (Scheme 1). While many of the isolated PPAPs retain the six-membered ring of their acylphloroglucinol progenitors, subsequent rearrangements and oxidative cleavages can result in ring expansions, contractions, or ring openings. In 2016, Tanaka, Kashiwada, and co-workers reported the isolation of two novel meroterpenoids with a contracted acylphloroglucinol-and a seco-acylphloroglucinol-derived motif, respectively, from the leaves of hypericum patalum. Whereas hypatulin A (2) has a highly oxygenated tricyclic octahydro-1,5-methanopentalene core, hypatulin B (3) possesses a bicyclo[3.2.1]octane motif. Both natural products have a densely substituted cyclopentane core bearing four stereocenters, three of them being quaternary (Scheme 1).