Oudemansins

Azoxystrobin is a synthetic analog of naturally occurring strobilurins and oudemansins. The preventative, curative, eradicant, translaminar and systemic properties facilitate control of a wide range of major plant pathogens in many crops... 

By the early 1980s, the in vitro activity of strobilurin A, the compound from Strobilurus tenacellus, and oudemansin A, from Oudemansiella mucida, had been completely characterised13 (Figure 4.23) and the mode of action was known to be the inhibition of electron transfer in complex... 

Ester homologation (11, 104).2 In an improved method for ester homologation via an a-bromo-a-keto dianion, an ester (RCO Hs) is treated sequentially with LiCHBr2, LiTMP (1 equiv.), and then an excess of BuLi to provide RC=C—OLi. Rearrangement occurs with complete retention of stereochemistry. This method provides a stereospecific synthesis of the antibiotic oudemansin (2). 

Anke T, Besl H, Mocek U, Steglich W (1983) Antibiotics from Basidiomycetes. XIII Strobilurin C and Oudemansin B, Two New Antifungal Metabolites from Xerula Species (Agaricales). J Antibiot 36 661... 

P-Methoxyacrylates. This is an important class of commercial fungicides based on a group of natural products, the strobilurins (see Fig. 10), such as strobilurin A and oudemansin A. Strobilurins act by inhibition of mitochondrial respiration. In 1996, the first representatives of this class of fungicide were launched, including azoxystrobin [52], In 1999, the first fluorine-containing strobilurin, trifloxystrobin (Flint ) [53], was launched by Syngenta and later acquired by Bayer for 760 million. 

This methodology has been applied to the synthesis of oudemansins by Kallmerten. In this example, the Wittig alkenation gave mixtures of ( )- and (Z)-products, as well as epimerizing the ether position. These problems were solved by acylating the phosphine oxide (239) and carrying out reduction and... 

Figure 4 The commercial synthetic agricultural fungicides azoxystrobin and kresoxim-methyl, inspired by the natural strobilurins, such as strobilurin A and oudemansin A...

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