Divergent Synthesis of Bioactive Resorcinols Isolated from the Fruiting Bodies of Hericium erinaceum: Total Syntheses of Hericenones A, B, and I, Hericenols B-D, and Erinacerins A and B

Total syntheses of 5'- and 7'-oxidized geranyl resorcylates isolated from the fruiting bodies of Hericium erinaceum and the submerged cultures of a Stereum species were achieved. The synthesis features derivatization of a suitably functionalized 5'-oxidized geranyl phthalide into a series of natural products by divergent functional group manipulations. Eight natural products including hericenones A, B, and I, hericenols B-D, and erinacerins A and B were synthesized (hericenol B and erinacerin B were synthesized as racemates). The structure of hericenone B was revised as the carbonyl regioisomer of the original assignment. In addition, this study indicated that hericenols C and D were artifacts resulting from degradation of hericenol B.