Tuning in : The reaction of halocyclopentane organometallic reagents can be tuned by the choice of metal (see scheme). Cyclopentylmagnesium bromide reduces aldehydes and ketones to the corresponding alcohols. However, in the presence of ZnCl2, normal Grignard addition to the ketones gives tertiary alcohols with complete diastereoselectivity. These protocols were used in the asymmetric synthesis of two medicinally important compounds.
The center of it all : An antitumor‐active trinuclear platinum complex forms unprecedented interstrand cross‐linked triadducts with 18‐mer DNA duplexes (see figure; complex in yellow with the platinum centers in red) and behaves differently from its dinuclear analogue.
Wheels on water? A waterwheel‐shaped porphyrin pentamer has been synthesized by palladium‐catalyzed cross‐coupling reactions. The key intermediate is a boronate porphyrin, in which four boronic ester groups are directly attached to the meso‐positions.
Piecing it together : The first total synthesis of naturally occurring diterpene pallavicinolide A was achieved. Notable features are highlighted by three key biomimetic transformations: a base‐promoted Grob fragmentation, a singlet oxygen oxidation, and an intramolecular Diels–Alder cycloaddition.
High pressure under the spotlight : A new milliliter‐scale reactor is developed for using supercritical CO2 to perform continuous photo‐oxidation reactions. Changing from a traditional microliter‐scale batch reaction to 8 hours of reaction using the new reactor gives a 3000‐fold scale‐up of the oxidation of α‐terpinene (see picture).
Tuning structures : We report a synthetically simple yet structurally rich gelator that self‐assembles through hydrogen bonding under different cooling regimes into different nanoscale morphologies (see figure), which can be covalently captured and stabilised by alkene metathesis.
