Synthetic studies towards the preparation of 2-benzyl-2-hydroxybenzofuran- 3(2H)-one, the prototype of naturally occurring hydrated auronols

Article abstract of DOI:10.1002/hlca.200490232

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.