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Syntheses of Optically Active Verrucarinic Acid. 40th Communication on Verrucarins and Roridins

✍ Scribed by Peter Herold; Peter Mohr; Christoph Tamm

Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
731 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Three syntheses of (2__S__, 3__R__)‐2,5‐dihydroxy‐3‐methylpentanoic acid (verrucarinic acid) and its derivatives suitably protected for the further transformation to macrocyclic trichothecenes are described. These involve an enantioselective ester hydrolysis by pig liver esterase, a Sharpless epoxidation and an asymmetric hydroboration.

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The compound should correctly be named apotrichothec-9-ene-3a, 13-diol, because apotrichothecane is the generic name for the skeleton [4]. We thank Dr. Ruegger, Specfrospin, Fallanden and Prof. H . Fritz, Ciba-Geipy AG, Basel, for recording the spectra and the helpful discussion.

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## Abstract The title compounds have been synthesized starting from verrucarol and diacetoxyscripenol (anguidine), (__E, Z__)‐muconic half ester and a derivative of verrucarinic acid. The latter has been prepared in optically active form from dimethyl 3‐methylglutarate.