1610729-75-3Relevant academic research and scientific papers
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
Kobayashi, Shoji,Tamanoi, Hidetsugu,Hasegawa, Yuichi,Segawa, Yusuke,Masuyama, Araki
, p. 5227 - 5238 (2014/06/23)
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. Our synthesis features derivatization of a suitably functionalized 5'-oxidized geranyl phthalide as a common intermediate, which was obtained by Stille coupling between the phthalide core and the side chain, into a series of natural products by divergent functional group manipulations. The crucial C5'-oxygen functionality was installed at the initial stage by alkylation by an α-cyano ethoxyethyl ether. From a common synthetic intermediate, eight total syntheses including hericenones A, B, and I, hericenols B-D, and erinacerins A and B were achieved (hericenol B and erinacerin B were synthesized as racemates). The structure of hericenone B established in the isolation paper was unambiguously revised as the carbonyl regioisomer at the lactam moiety.
