Synthetic Studies Towards the Preparation of 2‐Benzyl‐2‐ hydroxybenzofuran‐3(2 H )‐one, the Prototype of Naturally Occurring Hydrated Auronols | Zendy

Löser Reik | Zendy; Chlupacova Marta | Zendy; Marecek Ales | Zendy; Opletalova Veronika | Zendy; Gütschow Michael | Zendy

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Synthetic Studies Towards the Preparation of 2‐Benzyl‐2‐ hydroxybenzofuran‐3(2 H )‐one, the Prototype of Naturally Occurring Hydrated Auronols

Author(s) -

Löser Reik,

Chlupacova Marta,

Marecek Ales,

Opletalova Veronika,

Gütschow Michael

Publication year - 2004

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.200490232

Subject(s) - chemistry , ring (chemistry) , epoxide , combinatorial chemistry , base (topology) , benzofuran , benzyl alcohol , transformation (genetics) , stereochemistry , medicinal chemistry , organic chemistry , catalysis , mathematical analysis , biochemistry , mathematics , gene

Various synthetic approaches were employed to prepare 2‐benzyl‐2‐hydroxybenzofuran‐3(2 H )‐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(2 H )‐one (=aurone; 6 ) proved to be inappropriate, the hydrogenolytic epoxide‐ring opening of 2′‐phenylspiro[benzofuran‐2(3 H ),2′‐oxiran]‐3‐one ( 7 ), obtained from 6 , represents an efficient method to afford the auronol 8 .

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