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Synthetic Studies towards Pseurotin A. Part 3. Synthesis of a related highly functionalized γ-lactone

✍ Scribed by Zhuang Su; Christoph Tamm

Publisher
John Wiley and Sons
Year
1995
Tongue
German
Weight
866 KB
Volume
78
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A new general concept for the total synthesis of pseurotin A (1), a secondary metabolite of Pseudeurotium ovalis STOLK, which possesses a highly substituted 1‐oxa‐7‐azaspiro[4.4]nonane skeleton, is presented. A key intermediate of the planned reaction sequence is the functionalized γ‐lactone 8. The corresponding protected compound 52 was prepared using (S)‐O,O‐isopropylideneglyceraldehyde (13) and the bromoacetal 14 as starting material. γ‐Lactone 52 was obtained in enantiomerically pure state in ten steps. It possesses the desired configuration.

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Synthetic Studies Directed toward the Ps
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‐