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Biologically Active Metabolites from Fungi, 10. Generation of the Palmarumycin Spiroacetal Framework by Oxidative Cyclization of an Open Chain Metabolite fromConiothyrium palmarum

✍ Scribed by Krohn, Karsten ;Beckmann, Karsten ;Aust, Hans-Jürgen ;Draeger, Siegfried ;Schulz, Barbara ;Busemann, Stefan ;Bringmann, Gerhard


Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
367 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis


Abstract

The first “open chain” representative of the palmarumycins, the biaryl ether 1, was isolated from Coniothyrium palmarum. Phenol oxidation of 1 with silver oxide as a model for a biosynthetic step yielded 4 with the usual spiroacetal structure of the palmarumycins. The absolute (S)‐configuration of 4 (and thus of 1) was determined by quantumchemical CD calculations.