Camilla Corsi

A Convergent Approach toward the C1−C11 Subunit of Phoslactomycins and Formal Synthesis of Phoslactomycin B

The preparation of the C1-C11 subunit of phoslactomycins, and a formal synthesis of phoslactomycin B, were achieved by a convergent strategy involving the chelation-controlled addition of an alkynyl Grignard reagent to an alpha-alkoxy ketone. Catalytic enantioselective reductions of acetylenic ketones and a [2,3]-Wittig rearrangement were utilized as key steps to control the configuration of the C4, C5, and C9 stereocenters.

Phthalonitriles by hetero Diels-Alder reactions of 4,5-dicyanopyridazine with enamines: isolation and characterization of unprecedented intermediates

Abstract The title conversions were shown to involve as key intermediates new dicyanodiene systems, that can be isolated in high yields under mild conditions; their structures, inferred from analytical and spectral data, were confirmed by an X-ray study. Some improvements for the synthetic methodology connected with this finding are discussed.

Sedaxane, Isopyrazam and Solatenol™: Novel Broad-spectrum Fungicides Inhibiting Succinate Dehydrogenase (SDH) - Synthesis Challenges and Biological Aspects.

Sedaxane (SDX) 1, isopyrazam (IZM) 2 and Solatenol™ (STL) 3 are broad-spectrum pyrazole carboxamides, which originate from novel chemical classes of fungicides. Their mode of action (MoA) is inhibition of succinate dehydrogenase (SDH), which was recognized for a long time to deliver only compounds with a narrow biological spectrum. This view changed with the market introduction of BASFs boscalid in 2003. All major agro-companies subsequently worked in parallel on this MoA successfully and recently introduced new compounds to the market. Syngenta entered the SDHI area in 1998 and was able to introduce three complementary compounds to the market between 2010 and 2012. In this short review some synthesis challenges and biological effects of SDX 1, IZM 2 and STL 3 will be covered. New cost-efficient synthesis strategies for the preparation of o-biscyclopropyl-aniline, new benzonorbornene intermediates and the key pyrazole carboxylic acid intermediate which is essential for all three Syngenta SDHIs, will be in the focus of this review.Sedaxane (SDX) 1, isopyrazam (IZM) 2 and Solatenol™ (STL) 3 are broad-spectrum pyrazole carboxamides, which originate from novel chemical classes of fungicides. Their mode of action (MoA) is inhibition of succinate dehydrogenase (SDH), which was recognized for a long time to deliver only compounds with a narrow biological spectrum. This view changed with the market introduction of BASFs boscalid in 2003. All major agro-companies subsequently worked in parallel on this MoA successfully and recently introduced new compounds to the market. Syngenta entered the SDHI area in 1998 and was able to introduce three complementary compounds to the market between 2010 and 2012. In this short review some synthesis challenges and biological effects of SDX 1, IZM 2 and STL 3 will be covered. New cost-efficient synthesis strategies for the preparation of o-biscyclopropyl-aniline, new benzonorbornene intermediates and the key pyrazole carboxylic acid intermediate which is essential for all three Syngenta SDHIs, will be in the focus of this review.

Synthesis of fungicidally active succinate dehydrogenase inhibitors with novel difluoromethylated heterocyclic acid moieties

Novel fungicidally active succinate dehydrogenase inhibitors have been prepared, which either carry a difluoromethyl and methyl-bearing pyrazoline, pyrrole, or thiophene ring in the acid component, mimicking similar-substituted pyrazole carboxamides. As five-membered heterocyclic systems with such a special substitution pattern are barely known, unique synthesis routes had to be developed, which rely, e.g., on the van Leusen pyrrole synthesis and the halogen dance reaction. Synthesis and biological activity against selected Ascomycete pathogens of these difluoromethylated pyrazoline, pyrrole, and thiophene derivatives are reported.Graphical abstract