Synthesis and Detection of BODIPY-, Biotin-, and F- Labeled Single-Entity Dendritic Heparan Sulfate Mimetics.

Heparin and heparan sulfate (HS) are naturally occurring mammalian glycosaminoglycans, and their synthetic and semi-synthetic mimetics have attracted significant interest as potential therapeutics. However, understanding the mechanism of action by which HS, heparin, and HS mimetics have a biological effect is difficult due to their highly charged nature, broad protein interactomes, and variable structures. To address this, a library of novel single-entity dendritic mimetics conjugated to BODIPY, Fluorine-19 ( F), and biotin was synthesized for imaging and localization studies.

The curious yellow colouring matter of the Iceland poppy.

The pigment responsible for the yellow colour of the Iceland poppy (Papaver nudicaule) has fascinated chemists for decades. Named nudicaulin by Sir Robert Robinson in 1939, this flavoalkaloid has been the subject of several structural elucidation, biosynthesis, total synthesis and chemical ecology investigations. This account provides a chronological overview of the fascinating history of this natural product.

One-Pot, Tandem Wittig Hydrogenation: Formal C(sp)-C(sp) Bond Formation with Extensive Scope.

A one-pot, tandem Wittig hydrogenation of aldehydes with stabilized ylides is reported, representing a formal C(sp)-C(sp) bond construction. The tandem reaction operates under mild conditions, is high yielding, and is broad in scope. Chemoselectivity for olefin reduction is observed, and the methodology is demonstrated in the synthesis of lapatinib analogues and a formal synthesis of (±)-cuspareine.

Biomimetic synthesis of nudicaulins I and II, yellow pigments from the Iceland poppy Papaver nudicaule.

Indole and the anthocyanin orientalin proceed through a unique cascade sequence that leads to nudicaulins I and II in 92% yield. This biomimetic synthesis confirms the biosynthesis proposal for these structurally unprecedented flavoalkaloids that play a key role in the colour range displayed by the Iceland poppy.