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Synthetic Studies Directed toward the Pseurotins. Part I. Synthesis of Related Furan-3(2H)-ones

✍ Scribed by Matthys Dolder; Xie Shao; Christoph Tamm

Publisher
John Wiley and Sons
Year
1990
Tongue
German
Weight
335 KB
Volume
73
Category
Article
ISSN
0018-019X

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✦ Synopsis

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‐3(2__H__)‐one moiety of 1. The aldol condensation of the aldehyde 26, derived from D‐glucose, and the enolate of ketone 29 served as key reaction.

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Synthetic Studies Towards the Preparatio
Synthetic Studies Towards the Preparation of 2-Benzyl-2- hydroxybenzofuran-3(2H)-one, the Prototype of Naturally Occurring Hydrated Auronols
✍ Reik Löser; Marta Chlupacova; Ales Marecek; Veronika Opletalova; Michael Gütscho 📂 Article 📅 2004 🏛 John Wiley and Sons 🌐 German ⚖ 116 KB

## 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__)