Angewandte Chemie International Edition
© WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Cover Picture: Efficient Entry to the Hasubanan Alkaloids: First Enantioselective Total Syntheses of (−)-Hasubanonine, (−)-Runanine, (−)-Delavayine, and (+)-Periglaucine B (Angew. Chem. Int. Ed. 38/2011)
A unified synthetic strategy to prepare four hasubanan alkaloids, including hasubanonine (depicted), is described by S. B. Herzon et al. in their Communication on page 8863 ff. The synthesis features the application of 5-trimethylsilylcyclopentadiene as a removable, stabilizing stereocontrol element. This controlling group serves to set the absolute configuration in the products and is thermally cleaved at approximately 80 °C lower than the parent cyclopentadiene adducts.
Also of Interest
The Staudinger ligation has found numerous applications in complex biological systems, for example, for labeling glycans, lipids, DNA, and proteins. J. C. M. van Hest et al. show in their Review on page 8806 ff. the current status of this reaction.
Group 13 fluorides and (Ph3P)4N3 react in CH3CN to give the highly explosive M(N3)3·CH3CN adducts. R. Haiges, K. O. Christe et al. describe in their Communication on page 8828 ff. how excess azide leads to the anions [Ga(N3)5]2−, [In(N3)6]3−, and [Tl(N3)6]3−.
Engineering DNA Turnover
Isothermal DNA amplification is described by J. M. Gibbs-Davis et al. in their Communication on page 8922 ff. They show that introduction of destabilizing modifications into a DNA template leads to turnover in enzymatic ligation reactions.