Total Synthesis of the Antifungal Natural Product Mollisin

Mollisin, a bioactive polyketide secondary metabolite of the fungus Mollisia caesia, was synthesized in nine linear steps from commercially available 2,6-dimethyl-γ-pyrone. A key transformation in this first total synthesis of mollisin was the ipso substitution of an arylstannane, which permitted the otherwise cumbersome introduction of the characteristic dichloroacetyl moiety. The fungal fungicide was obtained in an overall yield of 9 %.

ChemInform Abstract: Total Synthesis of the Antifungal Natural Product Mollisin.

The title compound is synthesized in nine steps from commercially available 2,6-dimethyl-γ-pyrone in an overall yield of 9%.

Unexpected Formation of a 1,2-Dichloroacenaphthylene in a Friedel-Crafts Reaction with Chloral Hydrate

An unprecedented rearrangement was encountered during an attempted alkylation of an electron-rich naphthalene with chloral hydrate. The reaction produced a dichlorinated acenaphthylene and presumably involves the intermediate formation of a chloronium ion which is opened to produce the five-membered ring of the final product.

ChemInform Abstract: Unexpected Formation of a 1,2-Dichloroacenaphthylene in a Friedel-Crafts Reaction with Chloral Hydrate.

CCDC 945345: Experimental Crystal Structure Determination

Related Article: Sonja Schwolow, Horst Kunz, Joachim Rheinheimer, Till Opatz|2013|Eur.J.Org.Chem.|2013|6519|doi:10.1002/ejoc.201301088

CCDC 945347: Experimental Crystal Structure Determination

Related Article: Sonja Schwolow, Horst Kunz, Joachim Rheinheimer, Till Opatz|2013|Eur.J.Org.Chem.|2013|6519|doi:10.1002/ejoc.201301088

CCDC 945348: Experimental Crystal Structure Determination

Related Article: Sonja Schwolow, Horst Kunz, Joachim Rheinheimer, Till Opatz|2013|Eur.J.Org.Chem.|2013|6519|doi:10.1002/ejoc.201301088

CCDC 945346: Experimental Crystal Structure Determination

Related Article: Sonja Schwolow, Horst Kunz, Joachim Rheinheimer, Till Opatz|2013|Eur.J.Org.Chem.|2013|6519|doi:10.1002/ejoc.201301088