NeuO for Neuronal Labeling in Zebrafish.

We report the application of our newly developed fluorescent probe 3-(benzylamino)-4,4-difluoro-5-(4-propyl-1H-1,2,3-triazol-1-yl)-8-(4-(2-hydroxyacetamido)phen-yl)-4-bora-3a,4a-diaza-s-indacene (NeuO) to label and image live neurons in zebrafish. Immersing zebrafish embryos in NeuO or injecting NeuO into zebrafish brain ventricles results in nontoxic in vivo neuronal labeling. We demonstrate the applicability of NeuO and envisage the potential of this compound as a rapid and simple labeling reagent for studying neuron development and degeneration.

The Development of Novel Near-Infrared (NIR) Tetraarylazadipyrromethene Fluorescent Dyes.

Novel structures of an near-infrared (NIR) tetraarylazadipyrromethene (aza-BODIPY) series have been prepared. We designed the core structure containing two amido groups at the para-position of the aromatic rings. The amido group was incorporated to secure insensitivity to pH and to ensure a bathochromic shift to the NIR region. Forty members of aza-BODIPY compounds were synthesized by substitution of the acetyl group with commercial amines on the alpha bromide. The physicochemical properties and photostability were investigated and the fluorescence emission maxima (745~755 nm) were found to be in the near infrared (NIR) range of fluorescence.

Heteroatom-directed Wacker oxidations. A protection-free synthesis of (-)-heliophenanthrone.

The first enantioselective six-step synthesis of (-)-heliophenanthrone has been achieved without any protection-deprotection protocol at an overall yield of 28%. Key features of this synthesis comprise a heteroatom-directed Wacker oxidation of an internal cyclic olefin in addition to asymmetric Brown allylation and ring closing metathesis (RCM).

A diversity-oriented synthesis of bicyclic cis-dihydroarenediols, cis-4-hydroxyscytalones, and bicyclic conduritol analogues.

A common-intermediate-based enantioselective strategy has been developed aiming at bicyclic arene cis-dihydrodiols, cis-4-hydroxyscytalones, and bicyclic mimics of conduritol. Key features of this protocol include Barrett's asymmetric hydroxyallylation, ring-closing metathesis (RCM), and completely regioselective Wacker oxidation of internal cyclic olefins.