Formal synthesis of kibdelomycin and derivatisation of amycolose glycosides.

A convergent total synthesis of bacterial gyrase B/topoisomerase IV inhibitor kibdelomycin (a.k.a.

Divergent Synthesis of Six Recent Berkeleylactones.

The six recently isolated berkeleylactones E, J, K, M, N, and O were synthesized for the first time by a divergent strategy starting from a common intermediate in our synthesis of berkeleylactone A. Key features were the stereoselective formation of the γ,δ-dihydroxy-α,β-unsaturated ester moiety and the development of a general protection group strategy. Along the way we also established a short high-yielding formal synthesis of the often-synthesized antibiotic A26771B.

Synthesis of the fungal macrolide berkeleylactone A and its inhibition of microbial biofilm formation.

The fungal macrolide berkeleylactone A was synthesised in 13 steps and 24% yield using (R)-propylene oxide and an asymmetric Noyori hydrogenation of a β-ketoester to install the stereogenic centres. A domino addition-Wittig olefination of a 13-hydroxytetradecanal intermediate with the cumulated ylide Ph3PCCO closed the macrocyle by establishing the α,β-unsaturated ester group, necessary for the attachment of the sidechain thiol via a thia-Michael reaction. The synthetic berkeleylactone A inhibited the formation of Staphylococcus aureus biofilms and showed significant dispersive effects on preformed biofilms of Candida albicans by at least 45% relative to untreated controls at concentrations as low as 1.

Isolation of Borrelia miyamotoi and other Borreliae using a modified BSK medium.

Borrelia spirochetes are the causative agents of Lyme borreliosis (LB) and relapsing fever (RF). Despite the steady rise in infections and the identification of new species causing human illness over the last decade, isolation of borreliae in culture has become increasingly rare. A modified Barbour-Stoenner-Kelly (BSK) media formulation, BSK-R, was developed for isolation of the emerging RF pathogen, Borrelia miyamotoi.