Various synthetic approaches were employed to prepare 2‐benzyl‐2‐hydroxybenzofuran‐3(2H)‐one (8), the prototype of naturally occurring auronols. While the base‐induced ring transformation of 3‐hydroxyflavanone (2) as well as the hydration of 2‐benzylidenebenzofuran‐3(2H)‐one (=aurone; 6) proved to be inappropriate, the hydrogenolytic epoxide‐ring opening of 2′‐phenylspiro[benzofuran‐2(3H),2′‐oxiran]‐3‐one (7), obtained from 6, represents an efficient method to afford the auronol 8.

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