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

✍ Scribed by Reik Löser; Marta Chlupacova; Ales Marecek; Veronika Opletalova; Michael Gütschow

Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
116 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

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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Synthetic Studies Directed toward the Pseurotins. Part I. Synthesis of Related Furan-3(2H)-ones
✍ Matthys Dolder; Xie Shao; Christoph Tamm 📂 Article 📅 1990 🏛 John Wiley and Sons 🌐 German ⚖ 335 KB 👁 1 views

## Abstract According to a general concept for the total synthesis of pseurotin A (1), a secondary metabolite of __Pseudeurotium ovalis__ STOLK, 5‐[(1__S__,2__S__,__Z__)‐1,2‐dihydroxyhex‐3‐enyl]‐2,2,4‐trimethylfuran‐3(2__H__)‐one (17) was prepared. It is a model substance for the substituted furan‐